Trifluoroacetic acid → 2-[(4-chloro-benzyl)-pyrrolidin-3-yl-amino]-N-ethyl-acetamide

HRID 457204Notes

Reaction equation

HRID 457204 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:14][C:15](=[O:19])[NH:16][CH2:17][CH3:18])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][C:15]([NH:16][CH2:17][CH3:18])=[O:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667587503-[(4-Chloro-benzyl)-ethylcarbamoylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 231370142-[(4-chloro-benzyl)-pyrrolidin-3-yl-amino]-N-ethyl-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[(4-chloro-benzyl)-ethylcarbamoylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.12 g, 0.31 mmol) in dichloromethane cooled at 0° C. was treated with trifluoroacetic acid (20%) The resulting mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The combined organics were dried over sodium sulfate. The product was used without any further purification. ESI-MS m/z: 296 (M+1), UV retention time: 1.02 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. customThe product was used without any further purification

Sources & evidence

ORD record
ord-46927d2eac5b44d2b0572cdb4c928a2e
Source dataset
uspto-grants-2007_03
Patent number
US07186729B2

Reaction notes

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