Stannous Chloride → HCID 66758938, compound

HRID 1635523Notes

Reaction equation

HRID 1635523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:35])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([N+:32]([O-])=O)=[CH:31][C:18]3=4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Sn](Cl)Cl>CCO>[NH2:32][C:30]1[CH:29]=[CH:28][C:19]2[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:17](=[CH:16][CH2:15][CH2:14][N:11]3[CH2:10][CH2:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)([OH:35])[CH2:13][CH2:12]3)[C:18]=2[CH:31]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 53865477HCID 53865477, compound

Product 1

HCID 66758938HCID 66758938, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4—(4-chlorophenyl)-1-[3—(6,11-dihydro-2-nitrodibenz[b,e]oxepin-11-ylidene)propyl]piperidin-4-ol (120 mg) in EtOH (15 ml) were added tin (II) chloride (190 mg), and the mixture was heated to reflux for 1 hour. The solvent was distilled off under reduced pressure. To the residue was added ethyl acetate and sodium aqueous to neutralize. The organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with dichloromethane-methanol (95:5) to give the titled compound (70 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added ethyl acetate and sodium aqueous
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried with magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-f9368a9625c04f2f83c61196e3ee2244
Source dataset
uspto-grants-2003_01
Patent number
US06509346B2

Reaction notes

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