Water → 1-(2-(Diphenylphosphanyl)phenyl)-N,N-dimethylmethanamine

HRID 329654Notes

Reaction equation

HRID 329654 reaction equation
[CH3:1][N:2]([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[Cl-].[C:17]1([PH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CCCCCC.CCOCC>[C:24]1([P:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][N:2]([CH3:10])[CH3:1])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7681N,N-DimethylbenzylamineHCID 19695023Diphenylphosphane chlorideHCID 178418339Butyllithium

Product 1

HCID 113706101-(2-(Diphenylphosphanyl)phenyl)-N,N-dimethylmethanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A 15.0 ml portion of N,N-dimethylbenzenemethanamine and 300 ml of ether were mixed under a nitrogen atmosphere. A 58 ml portion of 2.6M butyl lithium in hexane was added and this mixture was stirred, under nitrogen for 30 hours. A mixture of 27.0 ml of diphenylphosphine chloride in 60 ml of ether was added dropwise and the mixture was stirred overnight. Water was added, the organic layer was separated and extracted twice with dilute hydrochloric acid. The combined acid extracts were basified with 10% sodium hydroxide, then extracted twice with ether. The ether extracts were combined, dried and evaporated, giving 15.9 of 2-(diphenylphosphino)-N,N-dimethylbenzenemethanamine as an oil.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred overnight
  3. customthe organic layer was separated
  4. extractionextracted twice with dilute hydrochloric acid
  5. extractionextracted twice with ether
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-e2a9aa8ab8c842959e5338220bffece6
Source dataset
uspto-grants-1990_01
Patent number
US04892885

Reaction notes

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