Aniline → 2-(4-dimethylamino-4-phenyl-cyclohexyl)-N-phenyl-acetamide

HRID 908994Notes

Reaction equation

HRID 908994 reaction equation
C([Li])CCC.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O[C:16](=[O:33])[CH2:17][CH:18]1[CH2:23][CH2:22][C:21]([N:30]([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)C.[Cl-].[NH4+]>C1COCC1>[CH3:32][N:30]([CH3:31])[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:22][CH2:23][CH:18]([CH2:17][C:16]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:33])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 67386781(4-Dimethylamino-4-phenyl-cyclohexyl)-acetic acid ethyl esterHCID 178418339Butyllithium

Product 1

HCID 116464442-(4-dimethylamino-4-phenyl-cyclohexyl)-N-phenyl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.6 M solution in hexane; 7.1 ml; 11.4 mmol) was added dropwise at 0° C. to a solution of aniline (0.53 g; 5.7 mmol) in 10 ml THF. The mixture was allowed to come to RT and was subsequently stirred for 1 h. A solution of (4-dimethylamino-4-phenyl-cyclohexyl)-acetic acid ethyl ester (1.5 g; 5.2 mmol) in 15 ml THF was added dropwise at −78° C. The mixture was subsequently stirred for 1 h and then allowed to come to RT. It was hydrolysed with ammonium chloride solution and extracted with MC. After concentration, the crude product was chromatographed on silica gel (eluent:ether). 308 mg (18%) of the less polar and 620 mg (36%) of the more polar diastereoisomer were obtained.

Workup

  1. customto come to RT
  2. stirringThe mixture was subsequently stirred for 1 h
  3. customto come to RT
  4. extractionextracted with MC
  5. concentrationAfter concentration
  6. customthe crude product was chromatographed on silica gel (eluent:ether)
  7. custom308 mg (18%) of the less polar and 620 mg (36%) of the more polar diastereoisomer were obtained

Sources & evidence

ORD record
ord-5bc8593a3cb0479aa7dc6291ceb75857
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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