Ethyl 4-(3-oxopropyl)piperidine-1-carboxylate → Ethyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 981621Notes

Reaction equation

HRID 981621 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1.[H][H]>[Ni].O1CCCC1>[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 14989197Ethyl 4-(3-oxopropyl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14989198Ethyl 4-(3-hydroxypropyl)piperidine-1-carboxylateYield 98.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 36 parts of ethyl 4-(3-oxopropyl)-1-piperidinecarboxylate and 450 parts of tetrahydrofuran was hydrogenated at normal pressure and at 20° C. with 2 parts of Raney nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in 260 parts of dichloromethane. The organic layer was washed with 100 parts of a diluted hydrochloric acid solution, dried, filtered and evaporated, yielding 36 parts (98.3%) of ethyl 4-(3-hydroxypropyl)-1-piperidinecarboxylate as a residue (int. 47).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in 260 parts of dichloromethane
  4. washThe organic layer was washed with 100 parts of a diluted hydrochloric acid solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-121fe17720b9415fb328a171314042cc
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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