Acetic Acid → HCID 14099726, compound

HRID 569466Notes

Reaction equation

HRID 569466 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:13](=[O:27])[CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.[BH4-].[Na+].C(O)(=O)C>CO>[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH:13]([OH:27])[CH2:14][N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride3×HCID 14099725HCID 14099725, compound

Product 1

HCID 14099726HCID 14099726, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 1 g of 1-[5-methyl-2-(3-pyridinyl)-1H-imidazol-4-yl]-2-(4-phenyl-1-piperazinyl)ethanone in 5 ml of methanol, cooled in an ice-water bath, was added 0.2 g of sodium borohydride. After gas evolution ceased, this mixture was stirred in the bath for 45 minutes, with the addition of 2 ml of methanol after 5 minutes, and then at room temperature for one hour. A 0.1 g portion of sodium borohydride was added, the mixture was stirred in the ice-water bath for 30 minutes, then at room temperature for one hour. The addition of 0.1 g of sodium borohydride and the reaction conditions were repeated twice more, then the mixture was poured into ice-water. The mixture was adjusted to pH 7-8 with glacial acetic acid. The gummy solid was collected, washed with water and then triturated with 30 ml of ether for 15 minutes. The ether was decanted and the solid triturated with 10 ml of fresh ether. The solid was collected, washed with ether and dried in vacuo, giving 0.6 g of the desired product as a pale yellow solid, mp 180°-184° C. (dec.).

Workup

  1. temperaturecooled in an ice-water bath
  2. waitat room temperature for one hour
  3. customthe reaction conditions
  4. customThe gummy solid was collected
  5. washwashed with water
  6. customtriturated with 30 ml of ether for 15 minutes
  7. customThe ether was decanted
  8. customthe solid triturated with 10 ml of fresh ether
  9. customThe solid was collected
  10. washwashed with ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-1a5f4dc33f9642dc88ed6d454a874fda
Source dataset
uspto-grants-1988_03
Patent number
US04732895

Reaction notes

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