Sodium Bicarbonate → HCID 14547358, compound

HRID 543125Notes

Reaction equation

HRID 543125 reaction equation
C(=O)(O)[O-].[Na+].[C:6]1([CH2:12][CH2:13][CH2:14][N:15]2[C:20](=[O:21])[CH2:19][N:18]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][C:16]2=[O:29])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+]>C(O)C>[C:6]1([CH2:12][CH2:13][CH2:14][N:15]2[C:16](=[O:29])[CH2:17][N:18]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH:20]2[OH:21])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 14547355HCID 14547355, compound

Product 1

HCID 14547358HCID 14547358, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

Saturated aqueous sodium bicarbonate solution (20 ml) was added to a solution of 1-(3-phenylpropyl)-4-benzyl-2,6-piperazinedione (5.35 g) in ethanol (170 ml) at 5° C. and sodium borohydride (1.23 g) added portionwise to the resulting mixture at 5° C. over a period of 2 h. The mixture was stirred for a further 1 h at 5° C. and the solvent removed in vacuo. Water (50 ml) was added, and the mixture extracted with dichloromethane (3×50 ml), the extracts washed with brine and dried (MgSO4). Evaporation of the solvent gave the title compound as a white solid (4.36 g, 81%)

Workup

  1. customthe solvent removed in vacuo
  2. additionWater (50 ml) was added
  3. extractionthe mixture extracted with dichloromethane (3×50 ml)
  4. washthe extracts washed with brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1f7cc4145fa84c4a9c4fe69450f32e88
Source dataset
uspto-grants-1987_04
Patent number
US04661489

Reaction notes

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