Acetic Anhydride → HCID 19085422, compound

HRID 962452Notes

Reaction equation

HRID 962452 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12][CH2:11]1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[O:18]([CH2:17][CH2:16][N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][NH:8][C:1](=[O:3])[CH3:2])[CH2:11][CH2:12]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 19085425HCID 19085425, compound

Product 1

HCID 19085422HCID 19085422, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Acetic anhydride (8.72 g) was added with stirring to a mixture of 4-aminomethyl-1-(2-phenoxyethyl)piperidine (20.0 g) in pyridine (85 ml) containing 4-dimethylaminopyridine (catalytic amount) with cooling to maintain ambient temperature. The mixture was stirred overnight at ambient temperature and then evaporated to dryness. Water was removed by adding toluene and removing the toluene by distillation. The residue was dissolved in water (100 ml) and 2M hydrochloric acid (50 ml). The solution was washed with dichloromethane, basified with concentrated sodium hydroxide solution and extracted with dichloromethane to give N-[1-(2-phenoxyethyl)piperid-4-ylmethyl]acetamide as an oil which solidified on standing, m.p. 79°-80° C.

Workup

  1. temperaturewith cooling
  2. customevaporated to dryness
  3. customWater was removed
  4. additionby adding toluene
  5. customremoving the toluene
  6. distillationby distillation
  7. dissolutionThe residue was dissolved in water (100 ml)
  8. washThe solution was washed with dichloromethane
  9. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-6eeffd14421443a4892566dfadd1ec6f
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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