Boron tribromide → 4-(4-Hydroxyphenyl)-1-(4-phenylbutyl)piperidine

HRID 1955227Notes

Reaction equation

HRID 1955227 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:17][CH2:18]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 98836884-(4-Methoxyphenyl)-1-(4-phenylbutyl)piperidine

Product 1

HCID 98181214-(4-Hydroxyphenyl)-1-(4-phenylbutyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared from BBr3 in CH2Cl2 (1 M, 3.75 mL) and 4-(4-methoxyphenyl)-1-(4-phenylbutyl)piperidine (323 mg, 1.00 mmol) in dry CH2Cl2 (20 mL) as a colorless crystalline solid (85 mg, 26%): mp 210-211° C., 1H NMR (CD3OD) 1.66-2.12 (m, 8H), 2.66-2.87 (m, 3H), 3.00-3.20 (m, 4H), 3.54-3.66 (m, 2H), 6.75 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.4 Hz, 2H), 7.14-7.32 (m, 5H).

Sources & evidence

ORD record
ord-5b485030253f4c328a287ccba5aae87e
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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