Acetyl chloride → 3-(Dimethylamino)-3'-methoxypropiophenone

HRID 2358477Notes

Reaction equation

HRID 2358477 reaction equation
[CH3:1][N+:2]([CH3:4])=[CH2:3].[I-].C(Cl)(=O)C.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)=[O:12]>C(#N)C>[CH3:3][N:2]([CH3:4])[CH2:1][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 114603-MethoxyacetophenoneHCID 2724133Dimethyl(methylene)ammounium iodide

Product 1

HCID 4328673-(Dimethylamino)-3'-methoxypropiophenoneYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The Eschenmoser salt was produced by reacting 232 g (2.27 mol, 1 equivalent) tetramethyl diaminomethane with 187 g (2.14 mol, 0.95 equivalent) acetyl chloride in 1200 ml acetonitrile. 328 g (2.17 mol, 0.96 equivalent) 3-methoxyacetophenone were then added within 115 minutes at a temperature of from +3° C. to +11° C. and then stirred at from +20° C. to +25° C. for 20 to 21 hours. The resulting hydrochloride salt of the 3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one (II) was filtered out. The residue was suspended in 1600 ml water and 190 ml sodium hydroxide solution (36% by weight) (pH 11-12) and extracted with 1000 ml ethyl acetate. The organic phase was separated off and dried over 50 g sodium sulfate. Once the organic solvent had been evaporated, the free base of the 3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one (II) was obtained as a colorless oil (93% yield, 96% purity ascertained by HPLC).

Workup

  1. filtrationThe resulting hydrochloride salt of the 3-dimethylamino-1-(3-methoxyphenyl)-propan-1-one (II) was filtered out
  2. extraction190 ml sodium hydroxide solution (36% by weight) (pH 11-12) and extracted with 1000 ml ethyl acetate
  3. customThe organic phase was separated off
  4. dry with materialdried over 50 g sodium sulfate
  5. customOnce the organic solvent had been evaporated

Sources & evidence

ORD record
ord-400d9256684944ab949a2678c9bb4980
Source dataset
uspto-grants-2010_07
Patent number
US07763754B2

Reaction notes

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