Ammonium Acetate → HCID 66822143, compound

HRID 2406576Notes

Reaction equation

HRID 2406576 reaction equation
C([BH3-])#[N:2].[Na+].[CH2:5]([N:7]([CH2:22][CH3:23])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=1)[CH3:6].C([O-])(=O)C.[NH4+]>CO.C(OCC)(=O)C>[CH2:5]([N:7]([CH2:22][CH3:23])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:2])[CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=1)[CH3:6]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 668223691-(4-(2-(Diethylamino)ethoxy)phenyl)butan-1-one

Product 1

HCID 66822143HCID 66822143, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Sodium cyanoborohydride (155 mg, 3.5 mmol) was added to a suspension of 1-(4-(2-(diethylamino)ethoxy)phenyl)butan-1-one (21; 186 mg, 0.7 mmol) and ammonium acetate (1.63 g, 21.2 mmol) in methanol (2 mL). The resulting mixture was then heated at 40° C. for 72 hours. The reaction mixture was diluted with ethyl acetate, washed with sat. aqueous NaHCO3 (2×) and sat. brine, dried over sodium sulfate and concentrated to give crude 25 (110 mg, 59%) as a yellow oil: MS (ES+) m/z 265.1 (M+H)+. This material was taken to the next step without further purification.

Workup

  1. washwashed with sat. aqueous NaHCO3 (2×) and sat. brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b01838df49f948cb8f3bc197c106841c
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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