Acetic Anhydride → HCID 86744809, compound

HRID 2051588Notes

Reaction equation

HRID 2051588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:15]([CH3:17])[OH:16])[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:18]([O:21]C(=O)C)(=[O:20])[CH3:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:15]([CH3:17])[OH:16])[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.[C:18]([O-:21])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 9878248HCID 9878248, compound

Product 1

HCID 86744809HCID 86744809, compound

Procedure

A mixture of 1.00 g of 4-(3'-chlorophenyl)-α,1-dimethyl-4-piperidinemethanol (Example 1) and 5 mL of acetic anhydride was heated under reflux for 90 minutes. Removal of the excess acetic anhydride and short-path distillation of the residue (170° bath temperature, 1 micron) gave 1.05 g of the title compound as an oil. NMR (CDCl3): δ7.1-7.4 (m,4H); 4.9 (quartet, J=7 Hz,1H); 2.8 (m,2H); 2.2 (s,3H); 2.0 (s,3H); 1.9-2.4 (m,6H); and 0.9 (d,J=7 Hz,3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. customRemoval of the excess acetic anhydride and short-path distillation of the residue (170° bath temperature, 1 micron)

Sources & evidence

ORD record
ord-c2b86e209f7049efb9cb650e9cae3a71
Source dataset
uspto-grants-1991_05
Patent number
US05019650

Reaction notes

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