Sodium borohydride → HCID 21919365, compound

HRID 1581948Notes

Reaction equation

HRID 1581948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][C:18](=[O:28])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18]([OH:28])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21919402HCID 21919402, compound

Product 1

HCID 21919365HCID 21919365, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of 1-{[4-(4-chlorophenyl)piperazin-1-yl]sulfonyl}-4-(5-chloropyridin-3-yl)butan-2-one (228 mg, 0.51 mmol) in a mixed solvent system of CH2Cl2/MeOH (1:1, 5 mL) at RT was added solid sodium borohydride in one portion. The reaction was stirred for 40 minutes before being quenched with aqueous hydrochloric acid (1 M, 2 mL). The layers were then separated and the aqueous phase extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried, (MgSO4), filtered and concentrated in vacuo. The crude product was then filtered through a plug of silica gel, eluting with 50% ethyl acetate in hexane to give the title compound (111 mg, 0.25 mmol).

Workup

  1. custombefore being quenched with aqueous hydrochloric acid (1 M, 2 mL)
  2. customThe layers were then separated
  3. extractionthe aqueous phase extracted with CH2Cl2 (3×5 mL)
  4. dry with materialThe combined organic extracts were dried, (MgSO4),
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe crude product was then filtered through a plug of silica gel
  8. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d8fd248bc7774bd5b4c014ee4cf7ad92
Source dataset
uspto-grants-2004_05
Patent number
US06734183B2

Reaction notes

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