Water → 3-(3,4-Dimethoxyphenyl)-1-ethylpiperidine

HRID 616029Notes

Reaction equation

HRID 616029 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH2:5]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 203708461-[3-(3,4-Dimethoxyphenyl)piperidin-1-yl]ethan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203708473-(3,4-Dimethoxyphenyl)-1-ethylpiperidineYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 680 mg of N-acetyl-3-(3',4'-dimethoxyphenyl)-piperidine in 10 ml of tetrahydrofouran was slowly added with stirring at 20° C to 200 mg of lithium aluminum hydride in 10 ml of tetrahydrofuran and the mixture was stirred for an hour and then cooled to 5° C. 10 ml of ethyl acetate were slowly added thereto and the mixture was poured into water and filtered. The aqueous phase was recovered by decanting and was extracted again with ethyl acetate. The combined organic phases were washed with water, dried and evaporated to dryness to obtain 600 mg of N-ethyl-3-(3',4'-dimethoxyphenyl)-piperidine melting at about 50° C.

Workup

  1. filtrationfiltered
  2. customThe aqueous phase was recovered
  3. customby decanting
  4. extractionwas extracted again with ethyl acetate
  5. washThe combined organic phases were washed with water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-92cbfc9bcd35494cbcbdb3676827e647
Source dataset
uspto-grants-1978_02
Patent number
US04072685

Reaction notes

Loading…