Water → ST048623

HRID 1248274Notes

Reaction equation

HRID 1248274 reaction equation
[CH:1]1([C:7]([N:9]2[CH2:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11](=[O:24])[CH2:10]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O.ClCCl>C(O)C>[CH:1]1([C:7]([N:9]2[CH2:10][C:11](=[O:24])[N:12]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:13]([OH:15])[CH2:14]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 702980HCID 702980, compoundHCID 4311764Sodium borohydride

Product 1

HCID 3337962ST048623Yield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.2 g (0.046 mol) of 4-(cyclohexylcarbonyl)-2,6-dioxo-1-phenethyl piperazine are dissolved in 600 ml of ethanol. In an inert atmosphere, at 0° C., there are added 8.7 g (0.0509 mol) of dihydrated cupric chloride and the mixture is left for 1 hour at 0° C. To the reaction medium, kept at 0° C., are added in portions 8.8 g (0.23 mol) of sodium borohydride and left for 45 minutes at 0° C. The excess of reducing agent is destroyed by adding acetone. The insoluble salts are filtered and the filtrate is evaporated to dryness. The residue obtained is treated with a mixture of water and dichloromethane. The organic phase is decanted, dried over dry sodium sulphate and evaporated to dryness. The residue which is obtained is purified by filtration on a silica bed (elutrient: ethyl acetate). Beige crystals, m.p.=134° C., yield: 73%.

Workup

  1. customkept at 0° C.
  2. waitleft for 45 minutes at 0° C
  3. customis destroyed
  4. additionby adding acetone
  5. filtrationThe insoluble salts are filtered
  6. customthe filtrate is evaporated to dryness
  7. customThe residue obtained
  8. customThe organic phase is decanted
  9. dry with materialdried over dry sodium sulphate
  10. customevaporated to dryness
  11. customThe residue which is obtained
  12. filtrationis purified by filtration on a silica bed (elutrient: ethyl acetate)

Sources & evidence

ORD record
ord-d7048f03ab7940a698d47ec077d4fb2c
Source dataset
uspto-grants-1985_06
Patent number
US04523013

Reaction notes

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