1,3-Dibromobenzene → HCID 22128305, compound

HRID 1858546Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCOCC>[CH2:14]([N:21]1[CH2:26][CH2:25][C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=2)([OH:27])[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: -75 °C

Procedure

A solution of 23.6 g (100 mmol) of 1,3-dibromobenzene in 250 ml of absolute ether was cooled to -75° C. A solution of 62.5 ml (100 mmol) of n-butyllithium (1.6M in hexane) was added dropwise within 45 minutes. The resulting suspension was stirred at -75° C. for 2.5 hours. Subsequently, a solution of 19.0 g (100 mmol) of 1-benzyl-4-piperidone in 100 ml of absolute ether was added dropwise within 30 minutes at -70° C. to -75° C. and thereafter the mixture was stirred for 2 hours. Subsequently, the mixture was partitioned between ether and saturated ammonium chloride solution, the organic phase was dried over magnesium sulphate and finally the solvent was removed under reduced pressure. The crude product was purified by chromatography on silica gel with a 1:1 mixture of methylene chloride and hexane as the eluent. There were obtained 28.3 g (82% of theory) of 1-benzyl-4-(3-bromophenyl)-piperidin-4-ol as a yellow oil; MS: 345, 347 (M)+.

Workup

stirringthe mixture was stirred for 2 hours
customSubsequently, the mixture was partitioned between ether and saturated ammonium chloride solution
dry with materialthe organic phase was dried over magnesium sulphate
customfinally the solvent was removed under reduced pressure
customThe crude product was purified by chromatography on silica gel with a 1:1 mixture of methylene chloride and hexane as the eluent

Sources & evidence

ORD record: ord-ea363c40b98442c6bf70be2c784290c0
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150526

Reaction notes

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