Ammonium Acetate → (rac)-4-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine

HRID 714097Notes

Reaction equation

HRID 714097 reaction equation
C([O-])(=O)C.[NH4+].[F:6][C:7]1[CH:8]=[C:9]([C:17]2[C:25]3[CH2:24][CH2:23][C:22](=O)[C:21]=3[CH:20]=[N:19][CH:18]=2)[CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14].C([BH3-])#[N:28].[Na+]>CO.C(O)C>[F:6][C:7]1[CH:8]=[C:9]([C:17]2[C:25]3[CH2:24][CH2:23][CH:22]([NH2:28])[C:21]=3[CH:20]=[N:19][CH:18]=2)[CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 898462884-(3-Fluoro-4-trifluoromethyl-phenyl)-5,6-dihydro-[2]pyrindin-7-one

Product 1

HCID 71811529(rac)-4-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of ammonium acetate (117 mg, 1.52 mmol) in MeOH (1 mL) was treated with 4-(3-fluoro-4-trifluoromethyl-phenyl)-5,6-dihydro-[2]pyrindin-7-one (intermediate A-14 [C1]) (15 mg, 0.051 mmol) dissolved in ethanol (0.5 mL) and the reaction mixture stirred at room temperature for 1 h. Sodium cyanoborohydride (11.2 mg, 0.18 mmol) was added and stirring continued at room temperature. After 15 min, the reaction mixture was heated to reflux for 30 min. The solvent was removed under reduced pressure, a sat. aq. solution of ammonium chloride (2 mL) and a 1 M solution of HCl (1 mL) were added and the aq. phase washed with dichloromethane (3×5 mL). To the aq. phase was added a 1 M solution of NaOH (2 mL) and extracted with dichloromethane (3×5 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure. The title compound was isolated as light brown solid (3.8 mg, 25%). MS: 297.4 (M+H)+.

Workup

  1. stirringstirring
  2. customcontinued at room temperature
  3. waitAfter 15 min
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for 30 min
  6. customThe solvent was removed under reduced pressure
  7. additiona sat. aq. solution of ammonium chloride (2 mL) and a 1 M solution of HCl (1 mL) were added
  8. washthe aq. phase washed with dichloromethane (3×5 mL)
  9. additionTo the aq. phase was added a 1 M solution of NaOH (2 mL)
  10. extractionextracted with dichloromethane (3×5 mL)
  11. dry with materialThe combined organic phases were dried over MgSO4
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2f0cb63cdb1498a812a1e9c40abf214
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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