1-(3-Chlorophenyl)piperazine monohydrochloride → HCID 69605145, compound

HRID 860000Notes

Reaction equation

BrC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.Cl.[Cl:29][C:30]1[CH:31]=[C:32]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:33]=[CH:34][CH:35]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(=O)(O)[O-].[Na+]>[Cl:29][C:30]1[CH:31]=[C:32]([N:36]2[CH2:41][CH2:40][N:39]([CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[CH2:38][CH2:37]2)[CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (647 mg, 1.44 mmol), 3-chlorophenyl-piperazine hydrochloride (1.0 g, 4.3 mmol) and diisopropylethylamine (0.75 mL, 4.3 mmol) in anhydrous DMSO (6 mL) were heated at 50° C. overnight. The cooled reaction mixture was diluted with saturated aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (3×30 mL), dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography on silica gel (5% MeOH/CH2Cl) afforded 280 mg (68%) of the desired product as a beige solid: mp 110–112° C.; MS (ESI) m/z nnn [M+H]+.

Workup

customThe cooled reaction mixture
extractionextracted with ethyl acetate (3×10 mL)
washThe combined organic layers were washed with brine (3×30 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a1fd0ceb75704c3a93e0eaafd3512f75
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153849B2

Reaction notes

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