2-Methoxyethanol → HCID 20218054, compound

HRID 236097Notes

Reaction equation

HRID 236097 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1>CS(C)=O>[ClH:8].[CH3:3][O:4][CH2:5][CH2:6][O:7][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)(=[O:16])=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 136079823-[(4-Chlorophenyl)sulfonyl]piperidine

Product 1

HCID 20218054HCID 20218054, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 1.56 g (0.065 mole) of sodium hydride and 5.32 g (0.07 mole) of 2-methoxyethanol in 300 ml of dimethylsulfoxide was stirred at room temperature for 0.5 hr. A solution of 12.0 g (0.0463 mole) of 3-[(4-chlorophenyl)sulfonyl]piperidine (free base) in 100 ml of dimethyl sulfoxide was added and the mixture was stirred at 80°-100° C. for 1 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and water. The methylene chloride layer was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil, the free base of the title compound. The free base was reacted with ethereal hydrogen chloride, crystallizing and recrystallizing using the solvent pair methanol-diethyl ether to give 10.12 g (65.2%) of the white crystalline hydrochloride salt, m.p. 206°-208° C.

Workup

  1. stirringthe mixture was stirred at 80°-100° C. for 1 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-da6619722c104c038a5d2f6d9fbcc233
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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