Acetic Acid → 4-(4-Methylphenyl)-3-phenylbutan-2-amine

HRID 1446419Notes

Reaction equation

HRID 1446419 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.C(O)(=O)C.C([BH3-])#[N:24].[Na+]>N.CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([NH2:24])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 126157934-(4-Methylphenyl)-3-phenylbutan-2-one

Product 1

HCID 222706534-(4-Methylphenyl)-3-phenylbutan-2-amine

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of the 4-(4-methylphenyl)-3-phenylbutan-2-one (308 mg, 1.29 mmol) in 7M ammonia in MeOH (5 mL) and acetic acid (3 mL) was added sodium cyanoborohydride (130 mg, 2.06 mmol) and the reaction stirred at room temperature overnight. The reaction was quenched by pouring into 2M sodium carbonate solution and extracted into EtOAc. The aqueous layer was salted and re-extracted. The combined organic extracts were dried over MgSO4 and concentrated to give the title compound as a mixture of 4 isomers which was used without further purification. LC-MS: m/e 240 (M+H)+ (2.22 min).

Workup

  1. customThe reaction was quenched
  2. additionby pouring into 2M sodium carbonate solution
  3. extractionextracted into EtOAc
  4. extractionre-extracted
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a67520b81ce44da0875a707b2fd1fdb9
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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