Potassium Carbonate → (S)-3-(3,3-dimethylbutan-2-ylamino)-1-(4-fluorophenyl)propan-1-one

HRID 403576

Reaction equation

HRID 403576 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5].C([O-])([O-])=O.[K+].[K+].[CH3:19][C:20]([CH3:25])([CH3:24])[C@@H:21]([NH2:23])[CH3:22]>C(#N)C>[CH3:19][C:20]([CH3:25])([CH3:24])[C@@H:21]([NH:23][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676722-Chloro-4'-fluoropropiophenoneHCID 7004913(2S)-3,3-dimethylbutan-2-amine

Product 1

HCID 58485266(S)-3-(3,3-dimethylbutan-2-ylamino)-1-(4-fluorophenyl)propan-1-oneYield 94.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-1-(4-fluorophenyl)propan-1-one (5.0 g, 0.027 mol) and K2CO3 (7.45 g, 0.054 mol) in acetonitrile (100 mL) was added (S)-3,3-dimethylbutan-2-amine (3.24 g, 0.032 mol), and the reaction mixture was stirred at rt overnight. The solution was filtered, and the filtrate was concentrated to give (S)-3-(3,3-dimethylbutan-2-ylamino)-1-(4-fluorophenyl)propan-1-one (6.40 g, 94%). 1H NMR (CDCl3): 0.82 (s, 9H), 0.91-0.96 (d, 3H), 2.14-2.22 (m, 1H), 2.73-2.82 (m, 1H), 3.01-3.11 (m, 3H), 7.01-7.09 (m, 2H), 7.88-7.96 (m, 2H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-885628af76954c99abdbbbd5319b3b71
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Linked notes

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