Ammonium Chloride → HCID 23138815, compound

HRID 1171752Notes

Reaction equation

HRID 1171752 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH:11]=[C:10](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:17][C:18]\2=[O:19])[CH:9]=[N:8]1)=[O:5])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH:11]=[C:10](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:16][CH2:17][CH:18]\2[OH:19])[CH:9]=[N:8]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23139093HCID 23139093, compound

Product 1

HCID 23138815HCID 23138815, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-3-{[1-(ethoxycarbonylmethyl)-1H-pyrazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (6.08 g) in ethanol (100 ml) was added sodium borohydride (230 mg). The resulting mixture was stirred at room temperature for 30 minutes, and the reaction was stopped by addition of a saturated aqueous ammonium chloride solution. The products were extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to afford the title compound as a yellow amorphous solid (6.2 g, yield: quantitative).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4e0147270fa44fa493a5e48aa74f66c8
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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