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Triethylamine → (r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine

HRID 411964
Notes
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Reaction equation

HRID 411964 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=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 69947237(r)-5,11-Dihydro-5-[1-(t-butoxycarbonyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine

Product 1

HCID 69200761(r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  3. stirringthe solution was stirred at room temperature for 30 minutes
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ab917076eae4a00a04f12091e7c133b
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562808B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes