Water → 2,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=O)[NH:10][CH2:9][CH2:8]1.O>O1CCCC1>[S:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][CH2:9][CH2:8]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a bottle containing a cooled suspension of lithium aluminum hydride (44 g, 1.17 mol) in dry tetrahydrofuran (1.5 L) was added 3,4-dihydro-1,4-benzothiazepin-5(2H)-one (150 g, 0.84 mol) in portions at 0° C. After being refluxed for 18 hours, the reaction mixture was cooled to 0° C., followed by addition of water (25 mL) dropwise. The reaction mixture was then filtered through a pad of celite and washed with dichloromethane. The filtrate was dried over sodium sulfate and evaporated in vacuo to afford 125 g of 2,3,4,5-tetrahydro-1,4-benzothiazepine (yield was 90%), which was used for the next step without further purification.
Workup
- additionTo a bottle containing
- temperatureAfter being refluxed for 18 hours
- filtrationThe reaction mixture was then filtered through a pad of celite
- washwashed with dichloromethane
- dry with materialThe filtrate was dried over sodium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-0b095e7833614b3db533cfd36b407b53
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871756B2
Reaction notes
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