Sodium hydride → (R)-7-chloro-5,11-dihydro-5-[1-(3,4-methylenedioxyphenethyl)pyrrolidin-2-ylmethyl]-dibenzo[b,e][1,4]oxazepine

HRID 2251879Notes

Reaction equation

HRID 2251879 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:18]=[CH:17][C:7]2[O:8][CH2:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[NH:12][C:6]=2[CH:5]=1.Cl[C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[CH2:21]1.C(=O)([O-])O.[Na+]>CCCCCC.CS(C)=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:18]=[CH:17][C:7]2[O:8][CH2:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]([CH2:24][C@H:23]3[CH2:25][CH2:20][CH2:21][N:22]3[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]4[O:34][CH2:35][O:36][C:30]=4[CH:29]=3)[C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 15481949(R)-3-chloro-1-(3,4-methylenedioxyphenethyl)piperidineHCID 218222787-Chloro-5,11-dihydrodibenzo[b,e][1,4]oxazepine

Product 1

HCID 59643983(R)-7-chloro-5,11-dihydro-5-[1-(3,4-methylenedioxyphenethyl)pyrrolidin-2-ylmethyl]-dibenzo[b,e][1,4]oxazepine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride (48 mg, 1.2 mmol) was washed with hexane in argon gas stream and then suspended in dimethyl sulfoxide (8 ml). The obtained suspension was stirred at room temperature for 30 minutes. 7-Chloro-5,11-dihydrodibenzo[b,e][1,4]oxazepine (232 mg, 1 mmol) was added to the suspension, and they were stirred at room temperature for 30 minutes and then at 50° C. for 30 minutes. A solution of (R)-3-chloro-1-(3,4-methylenedioxyphenethyl)piperidine (308 mg, 1.15 mmol) in dimethyl sulfoxide (3 ml) was added dropwise to the obtained solution, and they were stirred at 50° C. for 4 hours. The reaction mixture was distributed into saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with hexane and ethyl acetate (10:1) as the eluent, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-7-chloro-5,11-dihydro-5-[1-(3,4-methylenedioxyphenethyl)pyrrolidin-2-ylmethyl]-dibenzo[b,e][1,4]oxazepine in the form of a light yellow solid (362 mg, 78%).

Workup

  1. stirringwere stirred at room temperature for 30 minutes
  2. waitat 50° C. for 30 minutes
  3. stirringwere stirred at 50° C. for 4 hours
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. washAfter the elution with hexane and ethyl acetate (10:1) as the eluent, suitable fractions
  7. customwere collected
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e846c64d06244c168820fc07c0cb9c24
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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