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

HRID 2425988Notes

Reaction equation

HRID 2425988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][C:12]2[CH:13]=[C:14]([N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[CH:15]=[CH:16][C:17]=2[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][C:12]2[CH:13]=[C:14]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:15]=[CH:16][C:17]=2[C:18](=[O:23])[C:19]([F:20])([F:22])[F:21])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707254t-Butyl 4-(3-(1-(3,5-dichlorophenyl)ethylamino)-4-(2,2,2-trifluoroacetyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 866076571-(2-(1-(3,5-Dichlorophenyl)ethylamino)-4-(piperazin-1-yl)phenyl)-2,2,2-trifluoroethanone hydrochlorideYield 193.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 4-(3-(1-(3,5-dichlorophenyl)ethylamino)-4-(2,2,2-trifluoroacetyl)phenyl)piperazine-1-carboxylate (50.1 mg, 0.09 mmol) in dichloromethane (2.0 mL) was added a saturated solution of HCl in diethyl ether (15 mL). The reaction mixture was stirred for 2 hours. The solvent was removed by rotary evaporation to afford the title compound (42.0 mg, 95% yield). 1H NMR (400 MHz, CD3OD): δ 7.67 (d, 1H), 7.37 (s, 2H), 7.35 (s, 1H), 6.41 (d, 1H), 5.84 (s, 1H), 4.79 (m, 1H), 3.57 (m, 4H), 3.25 (m, 4H), 1.61 (d, 3H); MS (ESI) m/z: Calculated for C20H21Cl2F3N3O: 446.1; Observed: 446.5 (M++1) [corresponding to the free base].

Workup

  1. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-b9c35b011e154f08ae834c5edc87c76e
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

Loading…