Hydrochloric Acid → N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

HRID 1613277Notes

Reaction equation

HRID 1613277 reaction equation
[OH:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8](Cl)([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[O:24]1CCOCC1>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:22])[C:8]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([OH:24])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 15023452HCID 15023452, compound

Product 1

HCID 15023453N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

Conditions

Temperature
90 °C

Procedure

A solution of N-(4-hydroxy-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide (7.88 g) in a mixture of 1N-hydrochloric acid (85 ml) and 1,4-dioxane (180 ml) was heated at 90° C. for 45 minutes and evaporated in vacuo. To the residue was added water and extracted with ethyl acetate. The extract was washed successively with saturated sodium bicarbonate aqueous solution, water, and sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (5:1) as an eluent to give N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide as white powder (6.56 g).

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed successively with saturated sodium bicarbonate aqueous solution, water, and sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (5:1) as an eluent

Sources & evidence

ORD record
ord-e2ad47a59350496393fbd5a28e357067
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

Loading…