Acetic Anhydride → HCID 14986818, compound

HRID 2416917Notes

Reaction equation

HRID 2416917 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](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([O:16][CH:15]([CH3:17])[C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]1)(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 9878248HCID 9878248, compound

Product 1

HCID 14986818HCID 14986818, 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° C. bath temperature, 1 micron) gave 1.05 g of the title compound as an oil. 1H NMR (CDCl3): δ 7.1-7.4 (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° C. bath temperature, 1 micron)

Sources & evidence

ORD record
ord-23933f8a0ced4041b18ea2237fad193c
Source dataset
uspto-grants-2004_11
Patent number
US06825217B2

Reaction notes

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