Triethylamine → HCID 15572448, compound

HRID 1163890Notes

Reaction equation

HRID 1163890 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[CH3:14][O:15][C:16]1[CH:24]=[C:23]([NH2:25])[C:22]([Cl:26])=[CH:21][C:17]=1[C:18]([OH:20])=O.[CH:27]1([CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([NH2:40])[CH:36]([CH3:41])[CH2:35]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCCC1>[CH:27]1([CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([NH:40][C:18](=[O:20])[C:17]3[CH:21]=[C:22]([Cl:26])[C:23]([NH2:25])=[CH:24][C:16]=3[O:15][CH3:14])[CH:36]([CH3:41])[CH2:35]2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 20513279HCID 20513279, compound

Product 1

HCID 15572448HCID 15572448, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (2.78 ml; 0.02 moles) and ethyl chloroformate (1.9 ml; 0.02 moles) were added successively to a stirred suspension of 2-methoxy-4-amino-5-chlorobenzoic acid (4.0 g; 0.02 moles) in anhydrous tetrahydrofuran (150 ml) whilst maintaining the temperature between -5° and -10° C. After stirring at this temperature for half an hour, a solution of 1-cyclohexylmethyl-3-methyl-4-aminopiperidine (4.2 g; 0.02 moles) in anhydrous tetrahydrofuran (25 ml) was added and, after stirring for 1 hour at -5° to -10° C., the temperature was allowed overnight to reach room temperature. The solvent of the mixture was removed in vacuo, the residue poured into water, extracted with chloroform and the organic layers washed with water. The chloroformic solution was dried (Na2SO4) and the solvent removed in vacuo to give N-(1-cyclohexylmethyl-3-methylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide (3.5 g), m.p. 173°-176° C.

Workup

  1. temperaturewhilst maintaining the temperature between -5° and -10° C
  2. stirringafter stirring for 1 hour at -5° to -10° C.
  3. customto reach room temperature
  4. customThe solvent of the mixture was removed in vacuo
  5. additionthe residue poured into water
  6. extractionextracted with chloroform
  7. washthe organic layers washed with water
  8. dry with materialThe chloroformic solution was dried (Na2SO4)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0017beb5fff249909448cc3493f78734
Source dataset
uspto-grants-1983_01
Patent number
US04367232

Reaction notes

Loading…