Water → 5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine
Reaction equation
[S:1]1[C:5]2[C:6](=O)[NH:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.[BH4-].[Na+].O>O1CCCC1>[S:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 6.7 g of 4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one and 4.5 g of sodium borohydride in 70 ml of tetrahydrofuran was added boron trifluoride-ether complex dropwise under ice-cooling and the mixture was refluxed under heating for an hour. The mixture was poured into water, washed with chloroform, made alkaline with 10% potassium hydroxide solution and extracted with chloroform. The extract was washed with water, dried and concentrated to give 4.1 g of 5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine as an oil.
Workup
- additionwas added boron trifluoride-ether complex dropwise under ice-
- temperaturecooling
- temperaturethe mixture was refluxed
- temperatureunder heating for an hour
- washwashed with chloroform
- extractionextracted with chloroform
- washThe extract was washed with water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-881cec23a4264c1badec9b594daa163d
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05532240
Reaction notes
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