Boron tribromide → HCID 14480000, compound

HRID 231312Notes

Reaction equation

Cl.C[O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH2:16][CH2:15]1)[CH2:10][CH2:9]2.B(Br)(Br)Br>C(Cl)Cl>[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH2:16][CH2:15]1)[CH2:10][CH2:9]2

Participants

Conditions

Temperature: -78 °C

Procedure

1-(1,2,3,4-Tetrahydro-8-methoxy-2-naphthalenyl)-4-[3-(trifluromethyl)phenyl]piperazine hydrochloride (2.7 g, 6.0 mmole) was dissolved in 125 ml of methylene chloride and cooled to -78° C. in a dry ice/acetone bath. To the cold solution was added a mixture of 18.9 ml of 1 M boron tribromide and 25 ml of methylene chloride. The reaction was allowed to come to room temperature and stirred for three days. The reaction was quenched with methanol and concentrated in vacuo. The residue was column chromatographed on 100 g of silica gel with 5% methanol/chloroform as eluent and the crude title compound thus obtained was crystallized first from isopropanol with addition of 4 N isopropanolic HCl and then from acetone to yield 1.2 g of the title compound as the monohydrochloride, m.p. 207°-209° C.

Workup

additionTo the cold solution was added
customto come to room temperature
customThe reaction was quenched with methanol
concentrationconcentrated in vacuo
customchromatographed on 100 g of silica gel with 5% methanol/chloroform as eluent
customthe crude title compound thus obtained
customwas crystallized first from isopropanol with addition of 4 N isopropanolic HCl

Sources & evidence

ORD record: ord-01a836c0479649af826167accdbf2130
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845221

Reaction notes

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