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N-Benzylpiperidine-4-carboxaldehyde
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Name

N-Benzylpiperidine-4-carboxaldehyde

 EINECS 244-757-7
CAS No. 22065-85-6 Density 1.114 g/cm3
PSA 20.31000 LogP 2.03540
Solubility N/A Melting Point 315
Formula C13H17NO Boiling Point 299.5 °C at 760 mmHg
Molecular Weight 203.284 Flash Point 104.3 °C
Transport Information UN 2810 6.1/PG 3 Appearance colorless oil
Safety 26-28-36/37/39 Risk Codes 25-41
Molecular Structure Molecular Structure of 22065-85-6 (N-Benzylpiperidine-4-carboxaldehyde) Hazard Symbols ToxicT
Synonyms

Isonipecotaldehyde,1-benzyl- (8CI);1-Benzyl-4-formylpiperidine;1-Benzyl-4-piperidinecarboxaldehyde;4-Formyl-1-(phenylmethyl)piperidine;4-Formyl-1-benzylpiperidine;N-(Phenylmethyl)piperidine-4-carboxaldehyde;N-Benzyl-4-formylpiperidine;N-Benzyl-4-piperidinecarbaldehyde;

Article Data 32

N-Benzylpiperidine-4-carboxaldehyde Synthetic route

62718-31-4

1-benzylpiperidine-4-carbonitrile

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
Stage #1: 1-benzylpiperidine-4-carbonitrile With diisobutylaluminium hydride In toluene at 0℃; for 1h;
Stage #2: With water; sodium hydroxide In methanol; toluene for 0.5h; pH=8; Temperature;		97.5%
10315-06-7

1-benzyl-4-piperidinecarboxylic acid methyl ester

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
With red-aluminum/morpholine complex In toluene at -5 - 0℃; for 0.5h; Reagent/catalyst; Solvent; Inert atmosphere; Large scale;96.5%
Multi-step reaction with 2 steps
1: 69.5 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 50 °C
2: 94.3 percent / oxalyl chloride; dimethyl sulfoxide; Et3N / CH2Cl2 / 0.25 h / -55 °C
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol; sodium hydroxide / 2 h / Reflux
2.1: thionyl chloride / 2 h / Reflux
2.2: 0.5 h / Cooling with ice
3.1: thionyl chloride / 5 h / Reflux
4.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C
4.2: 0.5 h / pH 8
View Scheme
67686-01-5

1-benzyl-4-piperidinemethanol

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -70 - 20℃; Swern Oxidation;96%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -55℃; for 0.25h; Swern oxidation;94.3%
Stage #1: 1-benzyl-4-piperidinemethanol With dimethylsulfide; triethylamine In toluene at -15 - -10℃; Inert atmosphere;
Stage #2: With N-chloro-succinimide In toluene		85%
24228-40-8

N-benzyl isonipecotic acid ethyl ester

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane; toluene at -78℃; for 2.5h; Flow reactor;96%
With Red-ALP-KTB In various solvent(s) at 10℃;95%
Stage #1: N-benzyl isonipecotic acid ethyl ester With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667h; Inert atmosphere;
Stage #2: With lithium diisobutylmethoxy aluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;		94%
123-75-1

pyrrolidine

24228-40-8

N-benzyl isonipecotic acid ethyl ester

A

22065-85-6

1-benzyl-4-formylpiperidine

B

67686-01-5

1-benzyl-4-piperidinemethanol

C

N-benzyl-4-(pyrrolidin-1-ylmethyl)piperidine

D

N-benzyl-4-(pyrrolidin-1-ylcarbonyl)piperidine

Conditions
ConditionsYield
With Red-ALP In various solvent(s) at 20℃; for 2h;A 95%
B n/a
C n/a
D n/a
...Expand
503544-95-4

1-benzyl-1,2,3,6-tetrahydropyridine-4-carbaldehyde

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 3h;90%

1-benzyl-N,N-dimethylpiperidine-4-carboxamide

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
With sodium hydride; sodium iodide In tetrahydrofuran at 60℃; chemoselective reaction;75%
42790-44-3

1-benzyl-4-vinyl-piperidine

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
With PYRIMIDINE; sodium periodate; osmium(VIII) oxide In 1,4-dioxane; 2-methyl-propan-1-ol; water at 20℃; for 7h;74%

C14H16NO3(1-)*Na(1+)

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
Stage #1: C14H16NO3(1-)*Na(1+) With hydrogenchloride; water at 90℃; for 1.5 - 2h; Heating / reflux;
Stage #2: With ammonia In water at 15℃; pH=8.5 - 9.0; Product distribution / selectivity;		68%
3612-20-2

1-phenylmethyl-4-piperidone

18107-18-1

diazomethyl-trimethyl-silane

22065-85-6

1-benzyl-4-formylpiperidine

Conditions
ConditionsYield
Stage #1: diazomethyl-trimethyl-silane With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1.25h;
Stage #2: 1-phenylmethyl-4-piperidone In tetrahydrofuran at -78 - 20℃; for 4h; Heating / reflux;		55%
With N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide

N-Benzylpiperidine-4-carboxaldehyde Chemical Properties

Molecular Structure of N-Benzylpiperidine-4-carboxaldehyde (CAS NO.22065-85-6):

IUPAC Name: 1-benzylpiperidine-4-carbaldehyde 
Empirical Formula: C13H17NO
Molecular Weight: 203.2802
EINECS: 244-757-7
Sensitive: Air Sensitive
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 20.31 Å2
Index of Refraction: 1.6
Molar Refractivity: 62.4 cm3
Molar Volume: 182.3 cm3
Surface Tension: 51.1 dyne/cm
Density: 1.114 g/cm3
Flash Point: 104.3 °C
Enthalpy of Vaporization: 53.95 kJ/mol
Boiling Point: 299.5 °C at 760 mmHg
Vapour Pressure: 0.00119 mmHg at 25°C
InChI
InChI=1/C13H17NO/c15-11-13-6-8-14(9-7-13)10-12-4-2-1-3-5-12/h1-5,11,13H,6-10H2
Smiles
N1(Cc2ccccc2)CCC(C=O)CC1
Product Categories: pharmacetical; Alcohol Aldehyde & acid series; Piperidine; (intermediate of donepezil); Aromatics; Heterocycles; Building Blocks; Heterocyclic Building Blocks; Piperidines

N-Benzylpiperidine-4-carboxaldehyde Safety Profile

Hazard Codes: ToxicT
Risk Statements: 25-41
R25 :Toxic if swallowed. 
R41:Risk of serious damage to the eyes.
Safety Statements: 26-28-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
HazardClass: Irritant

N-Benzylpiperidine-4-carboxaldehyde Specification

  N-Benzylpiperidine-4-carboxaldehyde , with CAS number of 22065-85-6, can be called 4-piperidinecarboxaldehyde, 1-(phenylmethyl)- ; 1-Benzylpiperidin-4-carbaldehyd ; 1-Benzylpiperidine-4-carbaldehyde ; 1-Benzyl-4-piperidinecarboxaldehyde ; 1-Benzyl-4-piperidine-carboxaldehyde ; N-BenzylpiperN-Benzylpiperidine-4-carboxaldehyde . It is a kind of colorless oil.

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