Propionyl chloride → HCID 19085495, compound

HRID 962454Notes

Reaction equation

HRID 962454 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1>ClCCl.C(N(CC)CC)C>[O:16]([CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([CH2:7][NH:6][C:1](=[O:4])[CH2:2][CH3:3])[CH2:9][CH2:10]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 62324Propionyl chloride3×HCID 19085425HCID 19085425, compound

Product 1

HCID 19085495HCID 19085495, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of propionyl chloride (2.37 g) in dichloromethane (10 ml) was added dropwise to a solution of 4-aminomethyl-1-(2-phenoxyethyl)piperidine (6.0 g) in dichloromethane (50 ml) and triethylamine (3.9 ml) at 0° C. The solution was allowed to warm up to ambient temperature with stirring and then stirred at this temperature for a further 2 hours. More propionyl chloride (0.3 ml) was added at ambient temperature and the solution stirred for a further half-hour. Further propionyl chloride (0.3 ml) was added and the mixture stirred for 1 hour. The mixture was extracted with 2M hydrochloric acid. The combined acidic extracts were washed with ethyl acetate, then basified with sodium hydroxide solution and extracted with dichloromethane to give an oil which solidified on standing to give N-[1-(2-phenoxyethyl)piperid-4-ylmethyl]propionamide, m.p. 85°-86° C.

Workup

  1. stirringstirred at this temperature for a further 2 hours
  2. stirringthe solution stirred for a further half-hour
  3. stirringthe mixture stirred for 1 hour
  4. extractionThe mixture was extracted with 2M hydrochloric acid
  5. washThe combined acidic extracts were washed with ethyl acetate
  6. extractionextracted with dichloromethane
  7. customto give an oil which

Sources & evidence

ORD record
ord-96c7204524df46e089318314571dc84f
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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