The Journal of Organic Chemistry
Article
CDCl3) δ/ppm 147.6, 139.30, 137.4, 128.7, 127.4, 126.6, 105.7, 52.6,
13.5, 11.1. MS (ESI, +ve) m/z 187.1 [(M + H)+, 100%]. HRMS m/z
187.1224 [M + H]+ (calcd for C12H15N2, 187.1235). Data are
consistent with those reported in the literature.35
1-Benzylpyrrolidin-2-one 36. Column chromatography was
performed with EtOAc. Synthesis from benzyl chloride: colorless oil
(0.077 g, 88%). Synthesis from benzyl bromide: colorless oil (0.076 g,
87%). 1H NMR (400 MHz, CDCl3) δ/ppm 7.35−7.09 (m, 5H), 4.38
(s, 2H), 3.18 (t, J = 7.1 Hz, 2H), 2.36 (t, J = 8.1 Hz, 2H), 2.03−1.81
(m, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ/ppm 175.0, 136.7,
128.7, 128.2, 127.6, 46.7, 46.7, 31.0, 17.8, 17.7. MS (ESI, +ve) m/z
198.1 [(M + Na)+, 100%]. HRMS m/z 198.0909 [M + Na]+ (calcd
for C11H13NNaO, 198.0895). Data are consistent with those reported
in the literature.41
1-(1-Phenylethyl)pyrrolidin-2-one 37. Column chromatography
was performed with EtOAc:n-hexane (3:7) to give the product as
colorless plates (0.079 g, 84%). 1H NMR (400 MHz, CDCl3) δ/ppm
7.22 (m, 5H), 5.41 (q, J = 7.1 Hz, 1H), 3.36−3.17 (m, 1H), 2.90 (m,
1H), 2.50−2.26 (m, 2H), 1.84 (m, 2H), 1.44 (d, J = 7.1 Hz, 3H).
13C{1H} NMR (100 MHz, CDCl3) δ/ppm 174.4, 140.3, 128.5, 127.4,
127.0, 48.9, 42.3, 31.4, 17.9, 16.2. MS (ESI, +ve) m/z 212.1 [(M +
Na)+, 100%]. HRMS m/z 212.1045 [M + Na]+ (calcd for
C12H15NNaO, 212.1051). Data are consistent with those reported
in the literature.41
3,5-Dimethyl-1-(1-phenylethyl)-1H-pyrazole 30. Column chro-
matography was performed with EtOAc:n-hexane (1:4) to give the
product as a white solid (0.083 g, 83%). 1H NMR (400 MHz, CDCl3)
δ/ppm 7.24−7.09 (m, 3H), 7.04−6.99 (m, 2H), 5.74 (s, 1H), 5.26 (q,
J = 7.1 Hz, 1H), 2.20 (s, 3H), 2.00 (s, 3H), 1.82 (d, J = 7.0 Hz, 3H).
13C APT NMR (100 MHz, CDCl3) δ/ppm 147.1, 143.1, 139.1, 128.9,
127.7, 127.1, 125.7, 116.4, 55.0, 22.3, 13.4. MS (ESI, +ve) m/z 223.1
[[M + Na]+, 100%]. HRMS m/z 201.1383 [M + H]+ (calcd for
C13H17N2, 201.1391). Data are consistent with those reported in the
literature.36
9-Benzylcarbazole 31. Column chromatography was performed
with EtOAc:n-hexane (1:9). Synthesis from benzyl chloride: colorless
plates (0.100 g, 78%). Synthesis from benzyl bromide: white solid
(0.080 g, 62%). 1H NMR (400 MHz, CDCl3) δ/ppm 8.02 (d, J = 7.6
Hz, 2H), 7.45−6.89 (m, 11H), 5.35 (s, 2H). 13C{1H} NMR (100
MHz, CDCl3) δ/ppm 140.7, 137.3, 128.8, 127.5, 126.5, 125.9, 123.1,
120.5, 119.3, 109.0, 46.6. MS (ESI, +ve) m/z 258.1 [(M + H)+,
100%]. HRMS m/z 258.1287 [M + H]+ (calcd for C19H16N,
258.1283). Data are consistent with those reported in the literature.37
9-(1-Phenylethyl)-9H-carbazole 6. Column chromatography was
performed with EtOAc:n-hexane (1:9) to give the product as colorless
plates (0.091 g, 67%). 1H NMR (400 MHz, CDCl3) δ/ppm 8.01 (d, J
= 7.7 Hz, 2H), 7.36−6.96 (m, 11H), 5.95 (q, J = 7.1 Hz, 1H), 1.87 (d,
J = 7.1 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ/ppm 140.8,
139.9, 128.7, 127.4, 126.6, 125.5, 123.5, 120.4, 119.0, 110.2, 52.4,
17.5. MS (ESI, +ve) m/z 272.1 [(M + H)+, 100%]. HRMS m/z
272.1430 [M + H]+ (calcd for C20H18N, 272.1439). Data are
consistent with those reported in the literature.20
1-(4-Chlorobenzyl)-1H-benzo[d][1,2,3]triazole 45. Column chro-
matography was performed with EtOAc:n-hexane (3:7) to give the
1
product as colorless needles (0.104 g, 85%). H NMR (400 MHz,
CDCl3) δ/ppm 8.00 (d, J = 8.3 Hz, 1H), 7.50−7.21 (m, 5H), 7.13 (d,
J = 8.4 Hz, 2H), 5.74 (s, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ/
ppm 146.5, 134.7, 133.4, 132.8, 129.4, 129.1, 127.8, 124.2, 120.4,
109.6, 51.7. MS (ESI, +ve) m/z 266.0 [(M + Na)+, 100%]. HRMS m/
z 266.0465 [M(35Cl) + Na]+ (calcd for C13H1035ClN3Na, 266.0461).
Data are consistent with those reported in the literature.42
N-(4-Chlorobenzyl)benzamide 46. Column chromatography was
performed with EtOAc:n-hexane (3:7) to give the product as a white
solid (0.108 g, 88%). 1H NMR (400 MHz, CDCl3) δ/ppm 7.69 (dd, J
= 7.1, 1.7 Hz, 2H), 7.41 (td, J = 7.3, 1.7 Hz, 1H), 7.31 (td, J = 7.5, 1.7
Hz, 2H), 7.17 (tdd, J = 8.5, 6.3, 3.0 Hz, 4H), 6.71 (s, 1H), 4.55−4.37
(m, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ/ppm 166.5, 135.8,
133.1, 132.2, 130.6, 128.1, 127.7, 127.6, 126.0, 42.3. MS (ESI, +ve)
m/z 268.1 [(M(35Cl) + Na)+, 100%]. HRMS m/z 268.0536 [M(35Cl)
+ Na]+ (calcd for C14H1235ClNONa, 268.0505). Data are consistent
with those reported in the literature.43
1-Benzyl-2-methyl-1H-imidazole 32. Column chromatography
was performed with EtOAc:n-hexane (3:7). Synthesis from benzyl
chloride: appearance (0.076 g, 89%). Synthesis from benzyl bromide:
1
appearance (0.078 g, 90%). H NMR (400 MHz, CDCl3) δ/ppm
7.27−6.70 (m, 7H), 4.96 (s, 2H), 2.24 (s, 3H). 13C APT NMR (100
MHz, CDCl3) δ/ppm 136.5, 128.9, 127.9, 127.4, 126.6, 49.8, 13.1.
MS (ESI, +ve) m/z 195.1 [(M + Na)+, 100%]. HRMS m/z 173.1071
[M + H]+ (calcd for C11H13N2, 173.1078). Data are consistent with
those reported in the literature.38
1-(4-(Trifluoromethyl)benzyl)-1H-benzo[d][1,2,3]triazole 47. Col-
umn chromatography was performed with EtOAc:n-hexane (2:8) to
give the product as a white solid (0.110 g, 79%). 1H NMR (400 MHz,
CDCl3) δ/ppm 8.00 (d, J = 8.1 Hz, 1H), 7.50 (d, J = 8.1 Hz, 2H),
7.41−7.24 (m, 5H), 5.82 (s, 2H). 13C{1H} NMR (100 MHz, CDCl3)
2-Methyl-1-(1-phenylethyl)-1H-imidazole 33. Column chroma-
tography was performed with EtOAc:n-hexane (1:4) to give the
product as a colorless oil (0.085 g, 91%). 1H NMR (400 MHz,
CDCl3) δ/ppm 7.31−7.14 (m, 3H), 6.94 (m, 4H), 5.21 (q, J = 6.7
Hz, 1H), 2.20 (q, J = 3.3 Hz, 3H), 1.73 (d, J = 5.8 Hz, 3H). 13C APT
NMR (100 MHz, CDCl3) δ/ppm 144.9, 141.8, 129.0, 127.8, 127.2,
125.8, 116.5, 55.1, 22.4, 13.5. MS (ESI, +ve) m/z 209.1 [(M + Na)+,
100%]. HRMS m/z 187.1227 [M + H]+ (calcd for C12H15N2,
187.1235). Data are consistent with those reported in the literature.39
N-Benzylbenzamide 34. Column chromatography was performed
with EtOAc:n-hexane (2:3). Synthesis from benzyl chloride: white
solid (0.088 g, 83%). Synthesis from benzyl bromide: white solid
(0.081 g, 77%). 1H NMR (400 MHz, CDCl3) δ/ppm 7.91−7.49 (m,
2H), 7.49−7.10 (m, 8H), 6.66 (s, 1H), 4.51 (d, J = 5.9 Hz, 2H).
13C{1H} NMR (100 MHz, CDCl3) δ/ppm 167.6, 138.4, 134.5, 131.6,
128.8, 128.6, 128.0, 127.6, 127.1, 44.2. MS (ESI, +ve) m/z 234.1 [(M
+ Na)+, 100%]. HRMS m/z 212.1093 [M + H]+ (calcd for
C14H14NO, 212.1075). Data are consistent with those reported in
the literature.40
N-(1-Phenylethyl)benzamide 35. Column chromatography was
performed with EtOAc:n-hexane (1:4) to give the product as a white
solid (0.108 g, 96%). 1H NMR (400 MHz, CDCl3) δ/ppm 7.73−7.65
(m, 2H), 7.46−7.07 (m, 8H), 6.40 (d, J = 7.5 Hz, 1H), 5.25 (p, J =
7.1 Hz, 1H), 1.51 (d, J = 6.9 Hz, 3H). 13C{1H} NMR (100 MHz,
CDCl3) δ/ppm 166.6, 143.2, 134.6, 131.5, 128.8, 128.6, 127.5, 127.0,
126.3, 49.2, 21.8. MS (ESI, +ve) m/z 248.1 [(M + Na)+, 100%].
HRMS m/z 248.1051 [M + Na]+ (calcd for C15H15NNaO, 248.1051).
Data are consistent with those reported in the literature.41
2
1
δ/ppm 146.5, 138.9 (d, JC‑F = 1.8 Hz), 132.9, 130.9 (q, JC‑F = 32.7
2
3
Hz), 127.9, 127.9, 126.2 (q, J = 3.7 Hz), 124.3, 123.9 (q, J = 272.3
Hz), 120.4, 109.5, 51.6 MS (ESI, +ve) m/z 300.1 [(M + Na)+, 100%].
HRMS m/z 278.0911 [M + H]+ (calcd for C14H11N3F3, 278.0905).
Data are consistent with those reported in the literature.44
N-(4-(Trifluoromethyl)benzyl)benzamide 48. Column chromatog-
raphy was performed with EtOAc:n-hexane (2:8) to give the product
as colorless needles (0.113 g, 81%). 1H NMR (400 MHz, CDCl3) δ/
ppm 7.74−7.69 (m, 2H), 7.50 (d, J = 8.0 Hz, 2H), 7.46−7.40 (m,
1H), 7.35 (d, J = 8.1 Hz, 4H), 6.67 (t, J = 5.9 Hz, 1H), 4.59 (d, J = 6.0
Hz, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ/ppm 167.6, 142.4,
1
134.0, 131.8, 129.8 (q, JC‑F = 32.3 Hz), 128.7, 127.9, 127., 125.7 (q,
2JC‑F = 3.8 Hz), 122.7, 43.5. MS (ESI, +ve) m/z 302.1 [(M + Na)+,
100%]. HRMS m/z 302.0772 [M + Na]+ (calcd for C15H12F3NONa,
302.0769). Data are consistent with those reported in the literature.45
1-(Naphthalen-2-ylmethyl)-1H-benzo[d][1,2,3]triazole 49. Col-
umn chromatography was performed with EtOAc:n-hexane (2:8) to
give the product as a white solid (0.105 g, 81%). 1H NMR (400 MHz,
CDCl3) δ/ppm 8.08 (d, J = 7.8 Hz, 1H), 7.87−7.72 (m, 4H), 7.53−
7.46 (m, 2H), 7.36 (m, 4H), 6.00 (s, 2H). 13C{1H} NMR (100 MHz,
CDCl3) δ/ppm 146.4, 133.2, 133.1, 132.9, 132.2, 129.1, 127.9, 127.8,
127.5, 126.7, 126.7, 126.5, 125.0, 124.0, 120.1, 109.8, 52.5. MS (ESI,
+ve) m/z 282.1 [(M + Na)+, 100%]. HRMS m/z 282.1022 [M +
Na]+ (calcd for C17H13N3Na, 282.1007).
N-(Naphthalen-2-ylmethyl)benzamide 50. Column chromatog-
raphy was performed with EtOAc:n-hexane (2:8) to give the product
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J. Org. Chem. 2021, 86, 9723−9732