Ammonium Chloride → HCID 23138758, compound

HRID 1171667Notes

Reaction equation

HRID 1171667 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[C:11](/[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:10][N:9]=[N:8]1)=[O:4].[BH4-].[Na+].[Cl-].[NH4+]>ClCCl.CO>[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[C:11](/[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:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:16][CH2:17][CH:18]\2[OH:19])=[CH:10][N:9]=[N:8]1)=[O:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23138559HCID 23138559, compound

Product 1

HCID 23138758HCID 23138758, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(E)-3-({1-[2-(Methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-one (12.87 g) was dissolved in a mixed solvent of dichloromethane (100 ml) and methanol (100 ml). While the solution was being stirred at 0° C., sodium borohydride (480 mg) was added thereto. The resulting mixture was stirred at 0° C. for 30 minutes, and the reaction was stopped by addition of a saturated aqueous ammonium chloride solution. The product was extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to afford the crude title compound (13.22 g) as a pale yellow amorphous solid. This product was used in the next process without further purification.

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 30 minutes
  2. extractionThe product was extracted with dichloromethane
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-331311e9c071454cac1146602f627bf1
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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