Sodium borohydride → HCID 54435245, compound

HRID 1195674Notes

Reaction equation

HRID 1195674 reaction equation
[BH4-].[Na+].[C:3]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:28])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[C:3]([N:11]1[CH2:12][CH2:13][CH:14]([CH:17]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=2)[OH:28])[CH2:15][CH2:16]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 14011078HCID 14011078, compound

Product 1

HCID 54435245HCID 54435245, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.13 g, 30 mmol) was added to a stirred suspension of 1-benzoyl-4-(4-acetamidobenzoyl)piperidine (10.0 g, 29 mmol) in ethanol (300 ml), cooled in a water bath. The mixture was stirred at room temperature for 1 hour then additional sodium borohydride (1.13 g, 30 mmol) was added and stirring was continued for 2 hours. The solvent was evaporated under reduced pressure and water (200 ml), HCl--H2O (6M, 15 ml) and methanol (15 ml) were added. The mixture was extracted with dichloromethane (4×200 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure to give an off-white solid which was crystallized from ethanol to give the piperidine as white crystals. (5.77 g, 57%)

Workup

  1. temperaturecooled in a water bath
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. customThe solvent was evaporated under reduced pressure and water (200 ml), HCl--H2O (6M, 15 ml) and methanol (15 ml)
  5. additionwere added
  6. extractionThe mixture was extracted with dichloromethane (4×200 ml)
  7. dry with materialthe combined organic fractions were dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customto give an off-white solid which
  10. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-195f5f1dc36949b5b5b1a2b1ef93d8a8
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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