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

HRID 1910557Notes

Reaction equation

HRID 1910557 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-9446f1d03c8c499cbd035a542a4072fd
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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