Hydrochloric Acid → (1R,3S)-3-(2-Methoxyethyl)-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentanamine Dihydrochloride

HRID 270606Notes

Reaction equation

HRID 270606 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C@:5]1([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=3)[CH2:22][CH2:21]2)=[O:19])[CH2:9][CH2:8][C@@H:7]([NH:10]C(=O)OC(C)(C)C)[CH2:6]1.[ClH:36]>CCOCC>[ClH:36].[ClH:36].[CH3:1][O:2][CH2:3][CH2:4][C@:5]1([C:18]([N:20]2[CH2:21][CH2:22][N:23]([C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:29]=[CH:28][N:27]=3)[CH2:24][CH2:25]2)=[O:19])[CH2:9][CH2:8][C@@H:7]([NH2:10])[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59833567tert-Butyl [(1R,3S)-3-(2-methoxyethyl)-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentyl]carbamate

Product 1

HCID 68596205(1R,3S)-3-(2-Methoxyethyl)-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentanamine DihydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl [(1R,3S)-3-(2-methoxyethyl)-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentyl]carbamate (252 mg, 0.503 mmol) was dissolved in a 2 M solution of hydrogen chloride in ether (8 mL) and stirred at room temperature for 2 h. The reaction solution was concentrated to give the desird product as a yellow powder (0.36 g, 96%). MS calculated for C19H27F3N4O2 (M+H) 401.3; found 401.3.

Workup

  1. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-790c53ff660046a88d53e061244c96aa
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

Loading…