Borohydride → 1-(4-Methanesulphonamidophenyl)-4-[2-hydroxy-2-(4-methanesulphonamidophenyl)ethyl]piperazine

HRID 2291574Notes

Reaction equation

HRID 2291574 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=3)=[O:20])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[BH4-].[Na+].[BH4-]>C(O)C.CN(C)C=O.O>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([OH:20])[C:21]3[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=3)[CH2:16][CH2:17]2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

7

Reactant 3

HCID 28123BorohydrideHCID 4311764Sodium borohydride2×HCID 212789191-(4-Methanesulphonamidophenyl)-4-(4-methanesulphonamidophenacyl)piperazine

Product 1

HCID 212789221-(4-Methanesulphonamidophenyl)-4-[2-hydroxy-2-(4-methanesulphonamidophenyl)ethyl]piperazine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(4-Methanesulphonamidophenyl)-4-(4-methanesulphonamidophenacyl)piperazine [see Example 5(D)] (0.77 g) was dissolved in ethanol (3 ml) and dimethylformamide (5 ml). Sodium borohydride (0.125 g) was then added portionwise over 5 minutes, and the mixture was stirred for 21/2 hours at ambient temperature. A further 25 mg. sodium borohydride was then added and the reaction mixture was heated at 60° for 2 hours. A further 20 mg. of borohydride was added, and the reaction mixture was heated at 70° for 41/2 hours. The mixture was then diluted with water, precipitating the impure product containing some unreduced starting material (0.51 g after drying). This impure product was refluxed for 41/2 hours in ethanol (35 ml), adding sodium borohydride (110 mg) portionwise during the first 2 hours. The mixture was then evaporated, the residue washed with water, and crystallized from methanol, yield of the pure title compound 0.118 g., m.p. 230°-2° (dec.).

Workup

  1. temperaturethe reaction mixture was heated at 60° for 2 hours
  2. temperaturethe reaction mixture was heated at 70° for 41/2 hours
  3. customprecipitating the impure product
  4. additioncontaining
  5. customsome unreduced starting material (0.51 g after drying)
  6. temperatureThis impure product was refluxed for 41/2 hours in ethanol (35 ml)
  7. additionadding sodium borohydride (110 mg) portionwise during the first 2 hours
  8. customThe mixture was then evaporated
  9. washthe residue washed with water
  10. customcrystallized from methanol, yield of the pure title compound 0.118 g

Sources & evidence

ORD record
ord-7e1f6ae3dbcf4273b32d4beb5888fc05
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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