Hydrochloric Acid → HCID 18955939, compound

HRID 2379680Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH:5]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.C([Li])CCC.CN(C)[CH:30]=[O:31].Cl>O1CCCC1.CCCCCC>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:4]2[CH:20]=[CH:21][CH:22]=[C:2]([CH:30]=[O:31])[CH:3]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

1-(3-Bromo-4'-chlorobenzhydryl)-4-methylpiperazine (see U.S. Pat. No. 4,757,074) (1.00 g, 2.63 mmole) was dissolved in 12 ml of dry tetrahydrofuran under nitrogen and cooled to -78° C. A solution of 1.1 M n-butyllithium in hexane (2.4 ml) was added dropwise and the reaction was stirred for ten minutes. N,N-Dimethylformamide (0.25 ml, 3.2 mmole) was added in one portion and the reaction was allowed to warm to -40° C. Hydrochloric acid (1.0M, 20 ml) was added and the reaction was warmed to room temperature. The solution was washed with 20 ml of diethyl ether and the ethereal wash was discarded. The aqueous solution was made basic with aqueous sodium hydroxide and extracted with two 15 ml portions of chloroform. The combined chloroform extracts were dried over sodium sulfate and the solvent removed to give 738 mg of crude 1-(4-chloro-3'-formylbenzhydryl)-4-methylpiperazine as a dark oil.

Workup

temperatureto warm to -40° C
temperaturethe reaction was warmed to room temperature
washThe solution was washed with 20 ml of diethyl ether
washthe ethereal wash
extractionextracted with two 15 ml portions of chloroform
dry with materialThe combined chloroform extracts were dried over sodium sulfate
customthe solvent removed

Sources & evidence

ORD record: ord-bd3d815c664e46c68c79748597a7ac43
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364843

Reaction notes

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