Hydrochloric Acid → 3-(Dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride

HRID 1493581

Reaction equation

HRID 1493581 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[ClH:9].[CH3:10][NH:11][CH3:12].[CH2:13]=O.Cl>C(O)C.CC(C)=O>[ClH:9].[CH3:10][N:11]([CH3:13])[CH2:12][CH2:2][C:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 69202-AcetylthiopheneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 28768913-(Dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochlorideYield 155.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent2×

Procedure

A mixture of 2-acetylthiophene (63.1 g, 0.5 mol), dimethylamine hydrochloride (53.0 g, 0.65 mol), paraformaldehyde (19.8 g, 0.22 mol), and 12N hydrochloric acid (1 ml) in ethanol (80 ml) was refluxed for one and one-half hours. The solution was diluted with ethanol (100 ml) and acetone (500 ml). The solution was chilled overnight and the resulting solid was collected by filtration to yield 75.0 g (73%) of 3-dimethylamino-1-(2-thienyl)-1-propanone hydrochloride as a colorless crystalline solid. mp =182° C.-184° C.

Workup

  1. temperaturewas refluxed for one and one-half hours
  2. temperatureThe solution was chilled overnight
  3. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-84ab1556f112429aa3c3af0c90e4d4a4
Source dataset
uspto-grants-1991_06
Patent number
US05023269

Linked notes

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