1-Benzylpiperidine → HCID 19871348, compound

HRID 329657Notes

Reaction equation

HRID 329657 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[Cl-].[C:20]1([PH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCCCC.CCOCC>[C:27]1([P:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 761901-BenzylpiperidineHCID 19695023Diphenylphosphane chlorideHCID 178418339Butyllithium

Product 1

HCID 19871348HCID 19871348, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

An 8.77 g portion of 1-(phenylmethyl)piperidine was mixed with 200 ml of ether under argon. A 27 ml portion of 2.6N butyl lithium in hexane was added, this mixture was allowed to stand one hour, then a solution of 12.6 ml of diphenylphosphine chloride in 50 ml of ether was added dropwise. This mixture was stirred 48 hours, then the ether layer was separated, washed with water, then extracted twice with 100 ml of water containing 8 ml of hydrochloric acid followed by water. The aqueous extracts were combined, basified with 12 ml of 10N sodium hydroxide and extracted twice with ether. The ether extracts were combined and concentrated, giving 15.5 g of diphenyl[2-(1-piperidinylmethyl)phenyl]phosphine as an oil.

Workup

  1. customthe ether layer was separated
  2. washwashed with water
  3. extractionextracted twice with 100 ml of water containing 8 ml of hydrochloric acid
  4. extractionextracted twice with ether
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3cee3813fd44f939dad06e023075337
Source dataset
uspto-grants-1990_01
Patent number
US04892885

Reaction notes

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