Potassium Hydroxide → 1-[5-(2-Butylthioethyl) oxypentyl] azacycloheptane-2-one

HRID 1639124Notes

Reaction equation

HRID 1639124 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:14].[CH2:15]([S:19][CH2:20][CH2:21][OH:22])[CH2:16][CH2:17][CH3:18].[OH-].[K+]>CS(C)=O>[CH2:15]([S:19][CH2:20][CH2:21][O:22][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 792412-(Butylthio)ethanolHCID 146259321-(5-Bromopentyl) azacycloheptane-2-one

Product 1

HCID 146259331-[5-(2-Butylthioethyl) oxypentyl] azacycloheptane-2-oneYield 90.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5.24 g of 1-(5-bromopentyl) azacycloheptane-2-one, 1.34 g of 2-(n-butylthio) ethanol, 2.24 g of powderly potassium hydroxide and 30 ml of dimethylsulfoxide were mixed together, agitated at room temperature for 10 hours, extracted with dichloromethane to obtain an extract. The thus obtained extract was washed with water, dried, freed from the solvent by distillation off at reduced pressure and then finally distilled to obtain 2.84 g of colorless 1-[5-(2-butylthioethyl) oxypentyl] azacycloheptane-2-one having the following appearance, column temperature and analysis:

Workup

  1. extractionextracted with dichloromethane
  2. customto obtain an extract
  3. customThe thus obtained
  4. extractionextract
  5. washwas washed with water
  6. customdried
  7. distillationfreed from the solvent by distillation off at reduced pressure
  8. distillationfinally distilled

Sources & evidence

ORD record
ord-4dbf9d04999547dfa586da49d98c88b6
Source dataset
uspto-grants-1989_11
Patent number
US04882359

Reaction notes

Loading…