N,N'-Dicyclohexylurea → 3-Dimethylamino-1,1-diphenyl-propan-2-ol

HRID 866948Notes

Reaction equation

HRID 866948 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH:4]([OH:18])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH2:21]([N:23]([CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O>ClCCl>[CH2:30]([N:23]([CH2:21][CH3:22])[CH2:24][CH2:25][CH2:26][C:27]([O-:29])=[O:28])[CH3:31].[CH3:19][N:2]([CH3:1])[CH2:3][CH:4]([OH:18])[CH:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 125491223-Dimethylamino-1,1-diphenyl-propan-2-olHCID 137955394-(Diethylamino)butanoic acid hydrochloride

Product 2

HCID 125491223-Dimethylamino-1,1-diphenyl-propan-2-olHCID 203090674-Diethylaminobutyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-dimethylamino-1,1-diphenyl-propan-2-ol (2 55g) 4-diethylaminobutyric acid hydrochloride (1 95g.) and dicyclohexylcarbodiimide (2.1g.) in dichloromethane (50 ml) was stirred at room temperature for 5 days Dicyclohexylurea was filtered off and the filtrate concentrated. The residue was dissolved in dilute hydrochloric acid and ether. The acid extract was basified; isolation through ether in the normal manner gave an oil which was chromatographed as alumina (200g.). Elution with progressively graded mixtures of light petroleum and ether gave the 4-diethylaminobutyrate of 3-dimethylamino-1,1-diphenyl-propan-2-ol isolated as the dihydrochloride (41%) as a glass

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue was dissolved in dilute hydrochloric acid
  4. extractionThe acid extract
  5. customisolation through ether in the normal manner gave an oil which
  6. customwas chromatographed as alumina (200g.)
  7. washElution with progressively graded mixtures of light petroleum and ether

Sources & evidence

ORD record
ord-8a6e4c9499d947fca1c78b36b1648311
Source dataset
uspto-grants-1978_07
Patent number
US04101676

Reaction notes

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