Methanol → HCID 57287281, compound

HRID 648644Notes

Reaction equation

HRID 648644 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([CH:15]([C:25]([NH2:27])=[O:26])[C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28]O.S(=O)(=O)(O)O>ClCCCl>[CH3:28][O:21][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([CH:15]([CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH3:14])[C:25]([NH2:27])=[O:26])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20145110HCID 20145110, compound

Product 1

HCID 57287281HCID 57287281, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2 gm (5.46 m mol) of 4-[(1-(2-piperidinophenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid, 0.53 gm of methanol, 0.38 ml of conc. sulfuric acid, and 1.65 ml of 1,2-dichloro-ethane was refluxed for 24 hours, then evaporated in vacuo, dissolved in chloroform, and extracted with dilute sodium bicarbonate solution. The organic phase was washed with water, dried, filtered, and evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel (toluene/acetone=5:1).

Workup

  1. temperaturewas refluxed for 24 hours
  2. customevaporated in vacuo
  3. dissolutiondissolved in chloroform
  4. extractionextracted with dilute sodium bicarbonate solution
  5. washThe organic phase was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe evaporation residue was purified by column chromatography on silica gel (toluene/acetone=5:1)

Sources & evidence

ORD record
ord-b7106683cbda4aa2b9b35f7c7db631bb
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

Loading…