Diethyl Ether → 2-Methylbenzonitrile

HRID 1834182Notes

Reaction equation

[CH:1]1([CH2:7][CH:8]2CCCC[N:9]2CC(C2C=CC=C(Br)C=2)C)CCC[CH2:3][CH2:2]1.[CH2:24]([Li])CCC.C(O[CH2:32][CH3:33])C>>[CH3:24][C:33]1[CH:32]=[CH:3][CH:2]=[CH:1][C:7]=1[C:8]#[N:9]

Participants

Reactant 3

HCID 3283Diethyl Ether

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

HCID 178418339Butyllithium

Product 1

HCID 107212-Methylbenzonitrile

Procedure

Following a procedure similar to that described in Example 7. 18.9 g. (0.05 mole) of 2-cyclohexylmethyl-1-[2-(3-bromophenyl)propyl]piperidine was reacted with 0.095 mole of n-butyl lithium in diethyl ether and the resulting lithio derivative reacted directly with 12.4 g. (0.106 mole) of 2-methylbenzonitrile to give 4.85 g. of 2-cyclohexylmethyl-1-{2-[3-(2-methylbenzoyl)phenyl]propyl}piperidine as a yellow oil.

Sources & evidence

ORD record: ord-85f270f41cfb4c87baf4bab0eb6a4c70
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04069256

Reaction notes

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