Triethylamine → (r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine
Reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:20][N:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][O:24][C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]1=2)=O)(C)(C)C.C(N(CC)CC)C>O1CCOCC1>[NH:15]1[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:20][N:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][O:24][C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]1=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4 M hydrochloride/dioxane solution (1.5 ml) was added to a solution of 400 mg of (R)-5,11-dihydro-5-[1-(t-butoxycarbonyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine in dioxane (1.5 ml)), and the mixture was stirred at room temperature for one hour. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (20 ml). Triethylamine (0.16 ml, 1.1 mmol) was added to the obtained solution, and the solution was stirred at room temperature for 30 minutes and then washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound, i.e. (R)-5,11-dihydro-5-(2-pyrrolidinylmethyl)dibenzo [b,e][1,4]oxazepine, in the form of a light yellow oil(280 mg, 96%).
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in dichloromethane (20 ml)
- stirringthe solution was stirred at room temperature for 30 minutes
- washwashed with saturated aqueous sodium bicarbonate solution
- dry with materialThe organic layer was dried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-9ab917076eae4a00a04f12091e7c133b
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562808B1
Reaction notes
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