Chloromethyl Methyl Ether → 4,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chloride
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH2:8].[Cl:9][CH2:10]OC>CN(C)C=O>[ClH:9].[S:1]1[C:2]2[CH2:6][CH2:7][NH:8][CH2:10][C:3]=2[CH:4]=[CH:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 12.7 g (0.1 M) 2-(2-thienyl)ethylamine in 20 ml dimethylformamide heated at 55° C. are added, over 10 minutes, 8.05 g (0.1 M) chloromethylmethylether diluted in 10 ml dimethylformamide. After addition of the chloromethylmethylether, the medium is maintained at 70° C. for 2 hours, and is then cooled to room temperature. The desired product precipitates out and is rinsed with acetone, to give 5.5 g 4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine hydrochloride (M.p=225° C.; Yield: 31%).
Workup
- additionare added, over 10 minutes
- temperatureis then cooled to room temperature
- customThe desired product precipitates out
- washis rinsed with acetone
Sources & evidence
- ORD record
- ord-edffa91cfc1e41f8bcba666b2299c805
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04174448
Reaction notes
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