Triethylamine → N-ethyl-N-(1-benzylpiperid-4-yl)-2-methoxy-4-trifluoroacetylamino-5-chlorobenzamide

HRID 1163889Notes

Reaction equation

HRID 1163889 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[C:9]([Cl:19])=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH2:20]([N:27]1[CH2:32][CH2:31][CH:30]([NH:33][CH2:34][CH3:35])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CC(CC)=O>[CH2:34]([N:33]([CH:30]1[CH2:29][CH2:28][N:27]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:32][CH2:31]1)[C:5](=[O:6])[C:4]1[CH:8]=[C:9]([Cl:19])[C:10]([NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[CH:11][C:3]=1[O:2][CH3:1])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 106088761-benzyl-N-ethylpiperidin-4-amineHCID 128664055-Chloro-2-methoxy-4-(2,2,2-trifluoroacetamido)benzoyl chloride

Product 1

HCID 12866406N-ethyl-N-(1-benzylpiperid-4-yl)-2-methoxy-4-trifluoroacetylamino-5-chlorobenzamideYield 68.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of 2-methoxy-4-trifluoroacetylamino-5-chlorobenzoyl chloride (17.4 g; 0.055 moles) dissolved in anhydrous ethyl methyl ketone (75 ml) was added little by little to another solution of 1-benzyl-4-ethylamino-piperidine (10.9 g; 0.05 moles) and triethylamine (7.0 ml; 0.05 moles) in anhydrous ethyl methyl ketone (75 ml) at room temperature. On completion of the addition, the mixture was left at room temperature and stirred for 48 hours, and then the mixture was concentrated at reduced pressure, poured into water, and extracted with chloroform. The organic solution was dried (Na2SO4) and the solvent removed in vacuo. The residue was recrystallized from a mixture of methanol and diethyl ether to give N-ethyl-N-(1-benzylpiperid-4-yl)-2-methoxy-4-trifluoroacetylamino-5-chlorobenzamide (17 g), m.p. 198°-200° C.

Workup

  1. additionOn completion of the addition
  2. waitthe mixture was left at room temperature
  3. concentrationthe mixture was concentrated at reduced pressure
  4. additionpoured into water
  5. extractionextracted with chloroform
  6. dry with materialThe organic solution was dried (Na2SO4)
  7. customthe solvent removed in vacuo
  8. customThe residue was recrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-52cc650d413c420691798998c2b65158
Source dataset
uspto-grants-1983_01
Patent number
US04367232

Reaction notes

Loading…