Ammonium Acetate → HCID 14552584, compound

HRID 2248161Notes

Reaction equation

HRID 2248161 reaction equation
C([O-])(=O)C.[NH4+].C([BH3-])#[N:7].[Na+].[CH3:10][C:11]([CH3:26])=[CH:12][CH2:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21](=O)[CH3:22])=[CH:17][CH:16]=1>CO>[CH3:10][C:11]([CH3:26])=[CH:12][CH2:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]([NH2:7])[CH3:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 15662548HCID 15662548, compound

Product 1

HCID 14552584HCID 14552584, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonium acetate (3.29 g, 42.7 mmol), sodium cyanoborohydride (0.20 g, 3.0 mmol) and 3A molecular sieves are added to the above phenoxyacetone (1.0 g, 4.3 mmol) in 20 ml of anhydrous methanol under N2 and at RT. The reaction is stirred at RT for 4 days. The methanol is removed by rotoevaporation, and ether and water are added to the residue, followed by 10% NaOH. The mixture is extracted with ether (3X), and the combined organic layers are washed with water until neutral, dried and filtered and the solvent evaporated off to give 2-[4-(3-methyl-2-butenoxy)phenoxy]-1-methylethylamine.

Workup

  1. customThe methanol is removed by rotoevaporation, and ether and water
  2. additionare added to the residue
  3. extractionThe mixture is extracted with ether (3X)
  4. washthe combined organic layers are washed with water until neutral,
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated off

Sources & evidence

ORD record
ord-2bcf81eec21046e595e03489e129973b
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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