Diethyl Ether → Acetophenone

HRID 1834181Notes

Reaction equation

[CH:1]1([CH2:7][CH:8]2CCCCN2CC(C2C=CC=C(Br)C=2)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.C([O:31]CC)C>>[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:31])[CH3:8]

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 128050991-[2-(3-Bromophenyl)propyl]-2-(cyclohexylmethyl)piperidine

HCID 178418339Butyllithium

Product 1

HCID 7410Acetophenone

Procedure

Following a procedure similar to that described in Example 3, 37.8 g. (0.1 mole) of 2-cyclohexylmethyl-1-[2-(3-bromophenyl)propyl]piperidine was reacted with 0.18 mole of n-butyl lithium in diethyl ether and the resulting lithio derivative reacted directly with 27 g. (0.23 mole) of acetophenone to give 11.8 g. of 2-cyclohexylmethyl-1-{2-[3-(α-hydroxy-α-methylbenzyl)phenyl]propyl}piperidine as a yellow oil.

Sources & evidence

ORD record: ord-614d36dd6b33475c850998e8d0581a07
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04069256

Reaction notes

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