1-(Trifluoroacetyl)piperidine-4-carboxylic acid

Base Information

• Chemical Name: 1-(Trifluoroacetyl)piperidine-4-carboxylic acid
• CAS No.: 126501-70-0
• Molecular Formula: C8H10F3NO3
• Molecular Weight: 225.17
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID00404180
• Mol file: 126501-70-0.mol

Synonyms:126501-70-0;1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylic acid;1-(trifluoroacetyl)piperidine-4-carboxylic acid;1-(2,2,2-trifluoroacetyl)-4-piperidinecarboxylic acid;MFCD03840837;1-(TRIFLUOROACETYL)-4-PIPERIDINECARBOXYLIC ACID;4-PIPERIDINECARBOXYLIC ACID, 1-(2,2,2-TRIFLUOROACETYL)-;Bionet2_001569;C8H10F3NO3;N-TRIFLUOROACETYL ISONIPECOTIC ACID;SCHEMBL3285103;DTXSID00404180;HMS1368I13;AKOS000321385;AB16711;3-Carbomethoxy-4-piperidonehydrochloride;AM807551;SY082101;BB 0240466;CS-0038986;FT-0678922;EN300-298879;8W-0884;A906653;W-205252;1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylicacid;1-(Trifluoroacetyl)-4-piperidinecarboxylic acid, 95%;1-(2,2,2-Trifluoro-acetyl)-piperidine-4-carbox ylic acid;1-(2,2,2-trifluoroacetyl)-4-piperidinecarboxylic acid, AldrichCPR

Chemical Property of 1-(Trifluoroacetyl)piperidine-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.73E-07mmHg at 25°C
• Melting Point: 117 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• Refractive Index: 1.451
• Boiling Point: 386.6 °C at 760 mmHg
• PKA: 4.27±0.20(Predicted)
• Flash Point: 187.6 °C
• PSA: 57.61000
• Density: 1.43 g/cm³
• LogP: 0.80980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 225.06127767
• Heavy Atom Count: 15
• Complexity: 269

Purity/Quality:

98%min ^*data from raw suppliers

1-(2,2,2-Trifluoroacetyl)piperidine-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1C(=O)O)C(=O)C(F)(F)F

Technology Process of 1-(Trifluoroacetyl)piperidine-4-carboxylic acid

There total 2 articles about 1-(Trifluoroacetyl)piperidine-4-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

isonipecotic acid (498-94-2) + trifluoroacetic anhydride (407-25-0) → 1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylic acid (126501-70-0)

Guidance literature:

at 0 ℃; for 4h; Reflux;

DOI:10.1021/jacs.9b06643

Reference yield: 70.0%

isonipecotic acid (498-94-2) + trifluoromethylsulfonic anhydride (358-23-6) → 1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylic acid (126501-70-0)

Guidance literature:

In dichloromethane; at 0 ℃;

Reference yield:

1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylic acid (126501-70-0) → (4-{(4-Bromo-phenyl)-[(E)-ethoxyimino]-methyl}-4'-methyl-[1,4']bipiperidinyl-1'-yl)-(2,6-dimethyl-phenyl)-methanone

Guidance literature:

Multi-step reaction with 12 steps

1: SOCl₂ / Heating

2: AlCl₃ / 4 h / Heating

3: p-TsOH / Heating

4: 95 percent / aq. K₂CO₃ / methanol / 20 °C

5: Ti(OiPr)4 / 1,2-dichloro-ethane / 12 h / 20 °C

6: 7.3 g / 3 h / 20 °C

7: 98 percent / MeMgBr / tetrahydrofuran; diethyl ether / 2 h / 20 °C

8: 6 N HCl / ethyl acetate / 24 h / 20 °C

9: 5.1 g / 10percent aq. NaOH / 20 °C

10: NaOAc / methanol / 24 h / 20 °C

11: TFA / CH₂Cl₂ / 2 h / 20 °C

12: EDCI; iPr₂NEt; HOBT / CH₂Cl₂ / 12 h / 20 °C

With titanium(IV) isopropylate; hydrogenchloride; aluminium trichloride; thionyl chloride; methylmagnesium bromide; sodium acetate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; 2: Friedel-Crafts acylation;

DOI:10.1021/jm0200815

upstream raw materials:

isonipecotic acid

trifluoroacetic anhydride

trifluoromethylsulfonic anhydride

Downstream raw materials:

(3,4-dihydroisoquinolin-2(1H)-yl) (piperidin-4-yl)methanone

4-tert-butyl piperidine-4-carboxylate

4-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-piperidine

1-[4-(4-bromobenzoyl)piperidin-1-yl]-2,2,2-trifluoroethanone

Refernces

• 1、 Le, Ky Khac Anh,Nguyen, Hanh,Daugulis, Olafs. "1-Aminopyridinium Ylides as Monodentate Directing Groups for sp3 C-H Bond Functionalization". supporting information. p. 14728 - 14735. Retrieved 2019/10/11.
• 2、 -. "PIPERIDINE DERIVATIVES USEFUL AS CCR5 ANTAGONISTS". Page/Page column 30. . Retrieved 2010/02/12.