Acetic Acid → HCID 10803458, compound

HRID 1682667Notes

Reaction equation

HRID 1682667 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4][CH2:3]1.[C:15]([BH3-])#[N:16].[Na+].[C:19](O)(=O)[CH3:20].Cl>C(O)C>[CH2:15]([NH:16][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4][CH2:3]1)[C:20]1[CH:19]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 11984242Ethyl 3-(4-oxopiperidin-1-yl)propanoate

Product 1

HCID 10803458HCID 10803458, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Then, ethyl 3-(4-oxopiperidino)propionate (1.29 g, 6.47 mmol) sad benzylamine (0.85 ml, 7.78 mmol) were dissolved in ethanol (40 ml). A solution of sodium cyanoborohydride (256 mg, 4.22 mmol) dissolved in ethanol (20 ml) was added at room temperature sad acetic acid (1 ml) was further added to adjust its pH to 6-7. The mixture was stirred at room temperature for 18 hours sad added with concentrated hydrochloric acid (3 ml) to adjust the pH to 1-2. The resulting precipitate was collected by filtration and a saturated aqueous sodium hydrogencarbonate solution (150 ml) was added to adjust the mixture to pH 8-9. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure to give 1.39 g of ethyl 3-(4-benzylaminopiperidino)propionate as a colorless oil (74%). This oil (1.11 g, 3.82 mmol) was dissolved in ethanol (120 ml) and 10% palladium-carbon (320 mg) was added. The mixture was refluxed under heating for 5 hours under a hydrogen atmosphere. The reaction mixture was filtrated and low boiling matters were distilled away from the filtrate under reduced pressure to give 617 mg of ethyl 3-(4-aminopiperidino)propionate as a colorless oil (81%).

Workup

  1. additionwas further added
  2. filtrationThe resulting precipitate was collected by filtration
  3. additiona saturated aqueous sodium hydrogencarbonate solution (150 ml) was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration, low boiling matters
  8. distillationwere distilled away from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-08d75903ba7f4691a8ac7d055bae9a15
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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