Hydrochloric Acid → HCID 14835896, compound

HRID 1709263Notes

Reaction equation

HRID 1709263 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH:16]3[C:26]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][C:18]4[CH:27]=[CH:28][C:29]([O:31][Si](C(C)(C)C)(C)C)=[CH:30][C:17]3=4)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>C(O)C>[C:1]1(/[CH:7]=[CH:8]/[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH:16]3[C:26]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][C:18]4[CH:27]=[CH:28][C:29]([OH:31])=[CH:30][C:17]3=4)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14835780HCID 14835780, compound

Product 1

HCID 14835896HCID 14835896, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 1.05 g of 5-[4-{(E)-3-phenylallyl}piperazin-1-yl]-7-tert-butyldimethylsilyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridine. The solution was adjusted to pH 0.5 with 6 N hydrochloric acid and then stirred for 12 hours at room temperature. The reaction mixture was adjusted to pH 8.0 with a 10% aqueous sodium hydroxide solution. The solvent was removed by distillation under reduced pressure. To the residue were added 20 ml of water and 20 ml of ethyl acetate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/acetone=2/1) to obtain 600 mg of 5-[4-{(E)-3-phenylallyl}piperazin-1-yl]-7-hydroxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridine. It was recrystallized from ethanol to obtain 510 mg of colorless crystals having a melting point of 136°-140° C.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionTo the residue were added 20 ml of water and 20 ml of ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by a column chromatography (eluant: n-hexane/acetone=2/1)

Sources & evidence

ORD record
ord-51230146e8f44ccdb2d6ded1b8159a29
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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