Sodium borohydride → HCID 22628212, compound

HRID 278576Notes

Reaction equation

HRID 278576 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]3[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30]#[N:31])=[CH:24][CH:23]=3)[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[BH4-].[Na+]>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:32])[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]#[N:31])=[CH:24][CH:23]=3)[CH2:19][CH2:20]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54455617HCID 54455617, compound

Product 1

HCID 22628212HCID 22628212, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

4-(6-Chloronaphthalene-2-sulfonyl)-1-[4-(2-cyano-1-ethenyl)benzoyl]piperazine (699 mg) was dissolved in pyridine (15 ml) and methanol (5 ml), and to the mixture was added sodium borohydride (68 mg). The mixture was stirred at 60° C. for 2 hours and concentrated. To the residue was added diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate aqueous solution and brine in this order, dried and concentrated. The residue was purified with silica gel column chromatography (hexane: ethyl acetate=2:3) to give colorless crystals of the title compound (450 mg).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added diluted hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium bicarbonate aqueous solution and brine in this order
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography (hexane: ethyl acetate=2:3)

Sources & evidence

ORD record
ord-9a54fc3380864c5986396ab64643b588
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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