Hydrochloric Acid → 3-Dimethylamino-1-(5-methyl-2-thienyl)-propan-1-one hydrochloride

HRID 236558

Reaction equation

HRID 236558 reaction equation
[C:1]([C:4]1[S:5][C:6]([CH3:9])=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[ClH:10].[CH3:11][NH:12][CH3:13].[CH2:14]=O.Cl>C(O)C>[ClH:10].[CH3:11][N:12]([CH3:14])[CH2:13][CH2:2][C:1]([C:4]1[S:5][C:6]([CH3:9])=[CH:7][CH:8]=1)=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 836552-Acetyl-5-methylthiophene

Product 1

HCID 126434363-Dimethylamino-1-(5-methyl-2-thienyl)-propan-1-one hydrochlorideYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 10.0 grams (0.071 mole) of 2-acetyl-5-methylthiophene, 7.0 grams (0.086 mole) of dimethylamine hydrochloride, 2.5 grams of paraformaldehyde and 0.4 ml of concentrated hydrochloric acid in 10 ml of ethanol was heated under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure to a residual solid. The solid was recrystallized from methanol-diethyl ether to give 10.9 grams of 3-dimethylamino-1-(5-methyl-2-thienyl)propan-1-one hydrochloride; m.p. 145°-147° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a residual solid
  3. customThe solid was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-7533c9036b464e4a94d876df66df5f98
Source dataset
uspto-grants-1987_02
Patent number
US04645777

Linked notes

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