Trifluoroacetic acid → 2-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-1-butanamine hydrochloride

HRID 1880780Notes

Reaction equation

HRID 1880780 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]([CH2:22][CH3:23])[CH2:13][NH:14]C(=O)OC(C)(C)C)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[ClH:1].[Cl:1][C:2]1[C:3]([CH:12]([CH2:22][CH3:23])[CH2:13][NH2:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23078240Tert-butyl 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butylcarbamate

Product 1

HCID 667981942-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-1-butanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

146 g of tert-butyl 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butylcarbamate (0.414 mol) are dissolved in 2 L of dichloromethane. 190 mL of trifluoroacetic acid are added dropwise. The reaction mixture is stirred at room temperature for twelve hours, concentrated to dryness and diluted in 300 mL of hydrochloric acid 2M.

Workup

  1. concentrationconcentrated to dryness
  2. additiondiluted in 300 mL of hydrochloric acid 2M

Sources & evidence

ORD record
ord-3321531559074af4b1ba5ee3022a6065
Source dataset
uspto-grants-2012_11
Patent number
US08318777B2

Reaction notes

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