Ammonium Acetate → 1-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylamine

HRID 30232

Reaction equation

HRID 30232 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=O)[CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO>[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([NH2:29])[CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 525612731-[4-(4-Trifluoromethoxybenzyloxy)phenyl]ethanone

Product 1

HCID 586290281-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylamineYield 69.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 552.0 mg (1.779 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethanone and molecular sieves in 10 ml methanol were added 1679.0 mg (21.35 mmol) ammonium acetate and 78.0 mg (1.241 mmol) sodium cyanoborohydride and the reaction mixture was stirred 26 h (HPLC control) at 50° C. After cooling to room temperature, the molecular sieves were filtered off and washed with methanol. The solvent of the combined filtrates was evaporated and diethyl ether and water were added to the residue. While stirring the mixture was acidified with 6N aqueous HCl solution to pH2. The aqueous phase was separated and the organic phase was extracted two times with 1N aqueous HCl solution. Ethyl acetate was added to the combined aqueous phases and the mixture was basified with 6N NaOH to pH 10. The organic phase was separated and the aqueous phase was extracted two more times with ethyl acetate. The combined organic phases were dried over MgSO4 and the solvent evaporated at reduced pressure to afford 268.0 mg (0.861 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethylamine.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe molecular sieves were filtered off
  3. washwashed with methanol
  4. customThe solvent of the combined filtrates was evaporated
  5. additiondiethyl ether and water were added to the residue
  6. stirringWhile stirring the mixture
  7. customThe aqueous phase was separated
  8. extractionthe organic phase was extracted two times with 1N aqueous HCl solution
  9. additionEthyl acetate was added to the combined aqueous phases
  10. customThe organic phase was separated
  11. extractionthe aqueous phase was extracted two more times with ethyl acetate
  12. dry with materialThe combined organic phases were dried over MgSO4
  13. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-55298638a57f4a4094f88fe78e947bd1
Source dataset
uspto-grants-2008_09
Patent number
US07423060B2

Linked notes

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