Acetaminophen → HCID 21545601, compound

HRID 1605957Notes

Reaction equation

HRID 1605957 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Na].Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH:21]=[C:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1>C(O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][O:11][C:8]3[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=3)[CH2:18][CH:19]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 5360545SodiumHCID 21545599HCID 21545599, compound

Product 1

HCID 21545601HCID 21545601, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.3 g. of p-acetamidophenol are dissolved in a solution of 0.12 g. of sodium in 10 ml. of absolute ethanol and 0.55 g. of 1-(2-chloroethyl)-4 -(p-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride are added thereto all at once. The reaction mixture is heated under reflux conditions for 24 hours, filtered from the precipitated sodium chloride and the filtrate evaporated to dryness. The residue is absorbed on silica gel and eluted with methylene chloride-ether (1:1). The 4'-{2-[4-(p-fluorophenyl)-3,6-dihydro-1(2H)-pyridyl]-ethoxy}-acetanilide obtained from the eluate melts at 139°C. after recrystallization from acetic acid ethyl ester.

Workup

  1. temperatureThe reaction mixture is heated under reflux conditions for 24 hours
  2. filtrationfiltered from the precipitated sodium chloride
  3. customthe filtrate evaporated to dryness
  4. customThe residue is absorbed on silica gel
  5. washeluted with methylene chloride-ether (1:1)

Sources & evidence

ORD record
ord-2ab2b1217d9b44d3ac725980431c7ca7
Source dataset
uspto-grants-1976_04
Patent number
US03951987

Reaction notes

Loading…