Hydrochloric Acid → 3-(Dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride
Reaction equation
[ClH:1].[CH2:2]=O.Cl.[CH3:5][NH:6][CH3:7].[C:8]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)(=[O:10])[CH3:9]>CC(O)C>[ClH:1].[CH3:5][N:6]([CH3:2])[CH2:7][CH2:9][C:8]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)=[O:10]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
To a stirred solution of 37% HCl (0.60 mL, 19.8 mmol, 0.5 equivalents) in 2-propanol (73 mL) were added paraformaldehyde (3.00 gm, 95.1 mmol, 2.4 equivalents), dimethylamine hydrochloride (8.07 gm, 99.0 mmol, 2.5 equivalents) and 2-acetylthiophene (5.0 gm, 39.6 mmol) in sequence at room temperature. The cloudy suspension was heated to 70° C., gradually turning to a clear homogenous mixture. After approximately 18 h at 70° C. a white precipitate had formed. The reaction mixture was cooled to room temperature, and the white solid was filtered and washed with ice-cold ethanol (2×30 mL). The white solid was dried in a vacuum oven at 50° C. for 12 h to give 6.0 gm (69%) of 1 as a white solid.
Workup
- customAfter approximately 18 h at 70° C. a white precipitate had formed
- temperatureThe reaction mixture was cooled to room temperature
- filtrationthe white solid was filtered
- washwashed with ice-cold ethanol (2×30 mL)
- customThe white solid was dried in a vacuum oven at 50° C. for 12 h
Sources & evidence
- ORD record
- ord-147752c11c96417ba777a98d6cf7acf9
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233165B2
Reaction notes
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