1-[2-(3-Bromophenyl)propyl]-2-(cyclohexylmethyl)piperidine → 3-Tolunitrile

HRID 1649511Notes

Reaction equation

HRID 1649511 reaction equation
C1(CC2CCCC[N:9]2[CH2:14][CH:15]([C:17]2C=CC=C(Br)C=2)[CH3:16])CCCCC1.[CH2:24]([Li])[CH2:25][CH2:26][CH3:27]>C(OCC)C>[CH3:27][C:26]1[CH:16]=[C:15]([CH:17]=[CH:24][CH:25]=1)[C:14]#[N:9]

Participants

4

Reactant 2

HCID 128050991-[2-(3-Bromophenyl)propyl]-2-(cyclohexylmethyl)piperidineHCID 178418339Butyllithium

Product 1

HCID 121043-TolunitrileYield 212%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 3-methylbenzonitrile to give 10.7 g. of 2-cyclohexylmethyl-1-{2-[3-(3-methylbenzoyl)phenyl]propyl}piperidine as a yellow oil.

Sources & evidence

ORD record
ord-4de8f80dd2a34b3b9abf0404517cd634
Source dataset
uspto-grants-1983_11
Patent number
US04417052

Reaction notes

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