Sodium Chloride → (r)-5,11-Dihydro-5-[1-(4-pyrrolidinophenethyl)pyrrolidin-3-yl]dibenzo[b,e][1,4]oxazepine

HRID 2251904Notes

Reaction equation

HRID 2251904 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.CS(O[C@H:23]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:32][CH:31]=2)[CH2:24]1)(=O)=O.[Cl-].[Na+]>CCCCCC.CS(C)=O.C(OCC)(=O)C>[N:36]1([C:33]2[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][N:25]3[CH2:26][CH2:27][C@@H:23]([N:8]4[C:7]5[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=5[CH2:12][O:11][C:10]5[CH:14]=[CH:15][CH:16]=[CH:17][C:9]4=5)[CH2:24]3)=[CH:31][CH:32]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 59643988(S)-3-methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine

Product 1

HCID 12990605(r)-5,11-Dihydro-5-[1-(4-pyrrolidinophenethyl)pyrrolidin-3-yl]dibenzo[b,e][1,4]oxazepine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride (132 mg, 3.3 mmol) was washed with hexane in argon stream and then suspended in dimethyl sulfoxide (10 ml), and the obtained suspension was stirred at room temperature for 30 minutes. 5,11-Dihydrodibenzo[b,e][1,4]oxazepine (600 mg, 3.0 mmol) was added to the suspension, and they were stirred at room temperature for 30 minutes and then at 50° C. for additional 30 minutes. A solution of (S)-3-methanesulfonyloxy-1-(4-pyrrolidinophenethyl)pyrrolidine (340 mg, 1.0 mmol) in dimethyl sulfoxide (5 ml) was added dropwise to the obtained solution, and they were stirred at 50° C. for 42 hours. The reaction mixture was distributed into saturated aqueous sodium chloride 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 (3:1), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-5,11-dihydro-5-[1-(4-pyrrolidinophenethyl)pyrrolidin-3-yl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oily substance (142 mg, 32%).

Workup

  1. stirringwere stirred at room temperature for 30 minutes
  2. waitat 50° C. for additional 30 minutes
  3. stirringwere stirred at 50° C. for 42 hours
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. washAfter the elution with hexane and ethyl acetate (3:1), suitable fractions
  7. customwere collected
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9c06b4d3850740a29ca4d2cc70dd5443
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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