Pyridine → N,N-dimethyl-3-acetoxy-2-propylbenzylamine hydrochloride

HRID 275374Notes

Reaction equation

HRID 275374 reaction equation
Br.[CH3:2][N:3]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:7]=1[CH2:13][CH2:14][CH3:15])[CH3:4].N1C=CC=CC=1.[C:22]([Cl:25])(=[O:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.O.C(Cl)Cl>[ClH:25].[CH3:4][N:3]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:22](=[O:24])[CH3:23])[C:7]=1[CH2:13][CH2:14][CH3:15])[CH3:2]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 137809963-Dimethylaminomethyl-2-propylphenol hydrobromide

Product 1

HCID 13781008N,N-dimethyl-3-acetoxy-2-propylbenzylamine hydrochloride

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 83 g. of N,N-dimethyl-3-hydroxy-2-propylbenzylamine hydrobromide in 40 ml. of pyridine, 3 g. of 4-(dimethylamino)pyridine, and one liter of methylene chloride cooled by means of an external ice bath were added 32.3 ml. of acetyl chloride. After stirring two hours with cooling, 150 ml. of water were added and a solution was stirred an additional 30 minutes. The reaction was then treated with a large excess of a potassium carbonate solution and the layers were separated. The methylene chloride layer was washed with water, dried over sodium sulfate, and was evaporated in vacuo. The residue was distilled at 64°-77° C./0.01-0.04 torr to provide 65 g. of the free base of title product. The distillate was dissolved in 800 ml. of acetone, cooled, and treated with dry hydrogen chloride gas. After the solution was saturated, gas addition was stopped and one liter of diethyl ether was added. After standing overnight, the solution was filtered to provide 70.1 g. of the title product hydrochloride salt, m.p. 168°-173° C., NMR, IR.

Workup

  1. additionwere added 32.3 ml
  2. temperaturewith cooling
  3. stirringa solution was stirred an additional 30 minutes
  4. customthe layers were separated
  5. washThe methylene chloride layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customwas evaporated in vacuo
  8. distillationThe residue was distilled at 64°-77° C./0.01-0.04 torr
  9. customto provide 65 g

Sources & evidence

ORD record
ord-f5a7c00f8667470b87ee37be070e8ee6
Source dataset
uspto-grants-1995_02
Patent number
US05393768

Reaction notes

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