Sodium Chloride → HCID 69199696, compound

HRID 2251882Notes

Reaction equation

HRID 2251882 reaction equation
[H-].[Na+].[F:3][C:4]1[C:14]2[CH2:13][O:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[NH:9][C:8]=2[CH:7]=[CH:6][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]([N:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[CH2:21]1.[Cl-].[Na+].[CH3:39]CCCCC>CS(C)=O.C(OCC)(=O)C>[F:3][C:4]1[C:14]2[CH2:13][O:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[N:9]([CH2:39][C@H:23]3[CH2:24][CH2:25][CH2:20][CH2:21][N:22]3[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 24758Sodium hydrideHCID 59644011HCID 59644011, compoundHCID 69198926HCID 69198926, compound

Product 1

HCID 69199696HCID 69199696, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride (35 mg, 0.88 mmol) was washed with hexane in argon stream and then suspended in dimethyl sulfoxide (5 ml), and the obtained suspension was stirred at room temperature for 30 minutes. 1-Fluoro-5,11-dihydrodibenzo[b,e][1,4]oxazepine (0.17 g, 0.80 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 (R)-3-chloro-1-(4-dimethylaminophenethyl)piperidine (0.18 g, 0.80 mmol) in dimethyl sulfoxide (2 ml) was added dropwise to the obtained solution, and they were stirred at 50° C. for 6 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 (6:4) as the eluent, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (R)-1-fluoro-5,11-dihydro-5-[1-(4-dimethylaminophenethyl)piperidin-2-ylmethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oily substance (0.23 g, 64%).

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 6 hours
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. washAfter the elution with hexane and ethyl acetate (6:4) as the eluent, suitable fractions
  7. customwere collected
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-72704f10e8944cce94d06e2a69993013
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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