(3-Bromopropyl)benzene → 1-Benzyl-4-(3-phenylpropyl)piperidin-4-ol

HRID 380486Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Li]C(C)(C)C.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>CCOCC>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([OH:29])([CH2:2][CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 3.8 mL (25 mmol) of 1-bromo-3-phenyl propane in 200 mL of ether at −78° C. was slowly added 30 mL (50 mmol) of t-BuLi (1.7 M in pentane). The reaction mixture was warmed to −20° C. for 15 min, then it was recooled to −78° C. To this reaction mixture was slowly added a solution of 2.61 g (13.8 mmol) of 1-benzyl-4-piperidone in 20 mL of ether. After 15 min, the reaction mixture was poured into, 200 mL of sat'd NH4Cl solution. The reaction mixture was extracted with ethyl acetate and the combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4 filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 1:1) to give 3.3 g of the title compound.

Workup

customat −78° C.
customwas recooled to −78° C
extractionThe reaction mixture was extracted with ethyl acetate
washthe combined organic fractions were washed with sat'd NaCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by chromatography (silica, hexanes: ethyl acetate, 1:1)

Sources & evidence

ORD record: ord-cf6892b86a5141ed959c210795866f75
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303593B1

Reaction notes

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