Hydrochloric Acid → 1-(2-(3,5-Dimethoxybenzylamino)-4-(piperazin-1-yl)phenyl)-2,2,2-trifluoroethanone hydrochloride

HRID 2425999Notes

Reaction equation

HRID 2425999 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:34]=[C:35]([O:37][CH3:38])[CH:36]=1)[CH2:7][NH:8][C:9]1[CH:10]=[C:11]([N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH:12]=[CH:13][C:14]=1[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17]>C(OCC)C.ClCCl>[ClH:1].[CH3:38][O:37][C:35]1[CH:34]=[C:6]([CH:5]=[C:4]([O:3][CH3:2])[CH:36]=1)[CH2:7][NH:8][C:9]1[CH:10]=[C:11]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[CH:12]=[CH:13][C:14]=1[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707343Tert-butyl 4-(3-(3,5-dimethoxybenzylamino)-4-(2,2,2-trifluoroacetyl)-phenyl)piperazine-1-carboxylate

Product 1

HCID 671473271-(2-(3,5-Dimethoxybenzylamino)-4-(piperazin-1-yl)phenyl)-2,2,2-trifluoroethanone hydrochlorideYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A saturated solution of HCl gas in anhydrous diethyl ether was added portion wise to a solution of tert-butyl 4-(3-(3,5-dimethoxybenzylamino)-4-(2,2,2-trifluoroacetyl)-phenyl)piperazine-1-carboxylate (230 mg, 0.44 mmol) in anhydrous dichloromethane (1.5 mL). The resulting mixture was allowed to stand at room temperature for 30 min, and conversion was monitored by LCMS. The supernatant was pipetted out and the residue was concentrated down in vacuo and co-evaporated with diethyl ether to yield 150 mg (81%) of the title compound: 1H NMR (400 MHz, CD3OD): δ 7.65 (dd, 1H), 6.54 (d, 2H), 6.42-6.39 (m, 2H), 6.07 (d, 1H), 4.48 (br s, 2H), 3.76 (s, 6H), 3.63-3.60 (m, 4H), 3.30-3.25 (m, 4H). MS (ESI) m/z: Calculated: 423.18; Observed: 847.4 (2M++1)

Workup

  1. concentrationthe residue was concentrated down in vacuo and co-evaporated with diethyl ether

Sources & evidence

ORD record
ord-e56adfa5a60f4973be609ed480d8b80c
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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