Sodium Hydroxide → 9,10-dihydro-4-{-1[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]piperidin-4-ylidene}-4H-benzo-[4,5]cyclohepta[1,2-b]thiophene-10-ol

HRID 64641Notes

Reaction equation

HRID 64641 reaction equation
Br.[OH:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14](=[C:17]2[C:26]3[CH:25]=[CH:24][S:23][C:22]=3[C:21](=[O:27])[CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:13][CH2:12]1.[OH-].[Na+].[Na]>C(O)C>[OH:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][C:14](=[C:17]2[C:26]3[CH:25]=[CH:24][S:23][C:22]=3[CH:21]([OH:27])[CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 20236858HCID 20236858, compound

Product 1

HCID 202368569,10-dihydro-4-{-1[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]piperidin-4-ylidene}-4H-benzo-[4,5]cyclohepta[1,2-b]thiophene-10-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.8 g 4-{1-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]piperidin-4-ylidene}-4H-benzo[4,5]cyclohepta[1,2-b]thiophene-10(9H)one hydrobromide are added with stirring to a solution of 0.5 g sodium hydroxide in 100 ml ethanol. After 15 minutes, 0.45 g sodium borhydride are added in small portions and the mixture is agitated for 20 hours at room temperature. The solvent is then distilled off, the residue is taken up with water and with sodium hydroxide solution and extracted several times with chloroform. The combined extracts are then dried and evaporated, to give the title compound as a light yellow oil. The hydrogenofumarate of the title compound melts at 110°-113°.

Workup

  1. distillationThe solvent is then distilled off
  2. extractionextracted several times with chloroform
  3. customThe combined extracts are then dried
  4. customevaporated

Sources & evidence

ORD record
ord-d3cc3b0126674849b19e30db9c01020d
Source dataset
uspto-grants-1986_09
Patent number
US04609664

Reaction notes

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