1-[2-(3-Bromophenyl)propyl]-2-(cyclohexylmethyl)piperidine → 2,6-Dichlorobenzaldehyde

HRID 1660577Notes

Reaction equation

HRID 1660577 reaction equation
C1(CC2CCCCN2CC(C2C=CC=C([CH:23]([OH:32])[C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])C=2)C)CCCCC1.C1(CC2CCCCN2CC(C2C=CC=C(Br)C=2)C)CCCCC1.C([Li])CCC>C(OCC)C>[Cl:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:31])[C:24]=1[CH:23]=[O:32]

Participants

5

Reactant 3

HCID 128050991-[2-(3-Bromophenyl)propyl]-2-(cyclohexylmethyl)piperidineHCID 13409096HCID 13409096, compoundHCID 178418339Butyllithium

Product 1

HCID 67372,6-Dichlorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Cyclohexylmethyl-1-{2-[3-(α-hydroxy-2,6-dichlorobenzyl)phenyl]propyl}piperidine (yellow oil) prepared by reaction of 18.9 g. (0.05 mole) of 2-cyclohexylmethyl-1-[2-(3-bromophenyl)propyl]piperidine with 0.1 mole of butyl lithium in diethyl ether followed by 19.2 g. (0.11 mole) of 2,6-dichlorobenzaldehyde to give 19.3 g. of product.

Sources & evidence

ORD record
ord-9f925359d4df442d91c59091fa24fe9e
Source dataset
uspto-grants-1981_12
Patent number
US04308382

Reaction notes

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