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Sodium hydride → (r)-5,11-Dihydro-5-[1-[3-(4-methoxyphenyl)propyl]piperidine-2-ylmethyl]dibenzo[b,e][1,4]oxazepine

HRID 1859430
Notes
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Reaction equation

HRID 1859430 reaction equation
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[C@@H:19]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH2:20]1>CCCCCC.CS(C)=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][CH2:27][CH2:26][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]2[CH2:19][N:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=3[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]2=3)=[CH:34][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 22975047(r)-3-Chloro-1-[3-(4-methoxyphenyl)propyl]homopiperidine

Product 1

HCID 12018618(r)-5,11-Dihydro-5-[1-[3-(4-methoxyphenyl)propyl]piperidine-2-ylmethyl]dibenzo[b,e][1,4]oxazepine

Reagents, catalysts & solvents 4

HCID 679Dimethyl Sulfoxide
Solvent
2×
HCID 8058HexaneSolvent
HCID 8857Ethyl AcetateSolvent
HCID 516892Sodium BicarbonateSolvent

Procedure

60% Sodium hydride (39 mg, 0.99 mmol) was washed with hexane under argon atmosphere, and then suspended in dimethyl sulfoxide (6 ml). The obtained suspension was stirred at room temperature for 30 minutes. 5,11-Dihydrodibenzo[b,e][1,4]oxazepine (178 mg, 0.90 mmol) was added to the suspension, and they were stirred at room temperature for 20 minutes and then at 50° C. for 30 minutes. A solution of (R)-3-chloro-1-[3-(4-methoxyphenyl)propyl]homopiperidine (278 mg, 0.99 mmol) in dimethyl sulfoxide (3 ml) was added dropwise into the obtained solution, and they were stirred at 50° C. for 3 hours. The reaction liquid was distributed in saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduce pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with hexane and ethyl acetate (10:1) and then with hexane and ethyl acetate (3:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-5,11-dihydro-5-[1-[3-(4-methoxyphenyl) propyl]piperidine-2-ylmethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (196 mg, 49%).

Workup

  1. stirringwere stirred at room temperature for 20 minutes
  2. waitat 50° C. for 30 minutes
  3. stirringwere stirred at 50° C. for 3 hours
  4. customThe reaction liquid
  5. customThe organic layer was dried
  6. customthe solvent was evaporated
  7. washThe product was eluted with hexane and ethyl acetate (10:1)
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e0917c7f0923430190eea7e2f5d50c97
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06528504B2

Reaction notes

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