Dimethylamine → 1-Acetyl-3-(4-dimethylaminobenzoyl)piperidine

HRID 1756670Notes

Reaction equation

HRID 1756670 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=2)[CH2:5]1)(=[O:3])[CH3:2].[CH3:19][NH:20][CH3:21].C(=O)([O-])O.[Na+]>>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([N:20]([CH3:21])[CH3:19])=[CH:13][CH:12]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 21939813HCID 21939813, compound

Product 1

HCID 193908491-Acetyl-3-(4-dimethylaminobenzoyl)piperidine

Procedure

A mixture consisting of 2.49 g of 1-acetyl-3-(4-fluorobenzoyl)piperidine and 8 ml of 50% aqueous dimethylamine solution was stirred for 5 days at room temperature, followed by addition of a saturated aqueous solution of sodium hydrogen carbonate. The solution was extracted with ethyl acetate and the extract was dried. The solvent was then distilled off and the remaining oil was purified by silica gel column chromatography (eluent: ethyl acetate) to give 2.6 g of 1-acetyl-3-(4-dimethylaminobenzoyl)piperidine as a pale yellow oil.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. customthe extract was dried
  3. distillationThe solvent was then distilled off
  4. customthe remaining oil was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-75f1adb56d1c414e8b3ddc9499111275
Source dataset
uspto-grants-1995_08
Patent number
US05441967

Reaction notes

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