Hydrogen Bromide → 3-[1-(3-Phenylpropyl)piperidin-3-yl]phenol

HRID 1731880Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 15.2 g (0.049 mole) of 1-(3-phenylpropyl)-3-(3-methoxyphenyl)piperidine from Preparation 1 in 75 ml of glacial acetic acid was added 150 g of 48% aqueous hydrobromic acid. The reaction mixture was heated at 120° C. for 2.5 hours and then it was poured onto ice. The resulting mixture was basified with sodium carbonate and then it was extracted with ethyl acetate. The extracts were washed with water, followed by sodium chloride solution, and then they were dried and evaporated to give 17.2 g of crude product as a tan solid. Purification by recrystallization from a mixture of ethyl acetate/hexane/triethylamine (5:5:0.5) gave 4.0 g (28%) of the title compound, m.p. 119°-120° C.

Workup

additionit was poured onto ice
extractionit was extracted with ethyl acetate
washThe extracts were washed with water
customthey were dried
customevaporated
customto give 17.2 g of crude product as a tan solid
customPurification
customby recrystallization
additionfrom a mixture of ethyl acetate/hexane/triethylamine (5:5:0.5)

Sources & evidence

ORD record: ord-7d113b4781644b299fc0ead391523df2
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04623728

Reaction notes

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