Trifluoroacetic acid → [6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine

HRID 1835334Notes

Reaction equation

HRID 1835334 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:10]=[N:11][C:12]([Cl:22])=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])C)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:22][C:12]1[N:11]=[CH:10][C:9]([NH:7][CH3:6])=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 87890360[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 23502811[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.26 g (3.55 mmol) [6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester and 3.34 ml (42.8 mmol) trifluoroacetic acid in 11 ml dichloromethane was stirred at room temperature for 2 h. Addition of 2 M aqueous sodium carbonate solution was followed by extraction with two portions of dichloromethane. The combined organic layers were dried with sodium sulfate and concentrated to give 0.89 g (99%) of the title compound as an off-white solid.

Workup

  1. extractionwas followed by extraction with two portions of dichloromethane
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-642ba2decd6e4cd883cb6672781869e4
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

Loading…