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

HRID 1031992Notes

Reaction equation

HRID 1031992 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), dimethyl-amine 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-bb0f3527ff13483abce529d5eb594134
Source dataset
uspto-grants-1990_09
Patent number
US04956388

Reaction notes

Loading…