Acetyl chloride → HCID 21444477, compound

HRID 328257Notes

Reaction equation

HRID 328257 reaction equation
[C:1]1([C:7]2([OH:26])[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([NH2:24])[CH:20]=4)[C:15]3=[O:25])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:33](Cl)(=[O:35])[CH3:34]>C1C=CC=CC=1>[C:1]1([C:7]2([OH:26])[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([NH:24][C:33](=[O:35])[CH3:34])[CH:20]=4)[C:15]3=[O:25])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium Carbonate2×HCID 21444476HCID 21444476, compound

Product 1

HCID 21444477HCID 21444477, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3.5 g. of 2-(4-phenyl-4-hydroxypiperidinomethyl)-6-amino-1-tetralone are dissolved in 100 ml. of benzene. 5.3 g. of sodium carbonate are added and the mixture is cooled to 10° while a solution of 0.75 g. of acetyl chloride in 50 ml. of benzene is added dropwise at 10° with stirring. The mixture is stirred for 30 minutes. 5.3 g. more of sodium carbonate are added and the mixture is stirred for 3 hours more at 20°. It is then heated under reflux for 10 minutes, filtered and worked up in the customary manner. 2-(4-Phenyl-4-hydroxypiperidinomethyl)-6-acetamido-1-tetralone is obtained.

Workup

  1. temperaturethe mixture is cooled to 10° while a solution of 0.75 g
  2. stirringThe mixture is stirred for 30 minutes
  3. stirringthe mixture is stirred for 3 hours more at 20°
  4. temperatureIt is then heated
  5. temperatureunder reflux for 10 minutes
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d96fadb31a7a4333890a8908dfbdca1f
Source dataset
uspto-grants-1977_04
Patent number
US04016281

Reaction notes

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