Triethylamine → HCID 70414797, compound

HRID 622681Notes

Reaction equation

HRID 622681 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[CH2:14]([O:16][C:17]1[CH:25]=[C:24]([NH2:26])[C:23]([Cl:27])=[CH:22][C:18]=1[C:19]([OH:21])=O)[CH3:15].[O:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:33][N:34]1[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]1.[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45]>O1CCCC1.C(O)C>[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45].[O:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:33][N:34]1[CH2:35][CH2:36][CH:37]([NH:40][C:19](=[O:21])[C:18]2[CH:22]=[C:23]([Cl:27])[C:24]([NH2:26])=[CH:25][C:17]=2[O:16][CH2:14][CH3:15])[CH2:38][CH2:39]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 444972Fumaric AcidHCID 105366584-Amino-5-chloro-2-ethoxybenzoic acidHCID 167746731-(tetrahydrofuran-2-ylmethyl)piperidin-4-amine(SALTDATA: 2HCl 0.5H2O)

Product 1

HCID 70414797HCID 70414797, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (5.6 ml; 0.04 moles) and ethyl chloroformate (3.84 ml; 0.04 moles) were added successively to a stirred suspension of 2-ethoxy-4-amino5-chlorobenzoic acid (8.6 g; 0.04 moles) in anhydrous tetrahydrofuran (300 ml) whilst maintaining the temperature between -5° and -10° C. After stirring at this temperature for 0.5 hours, a solution of 1-(2-tetrahydrofurylmethyl)-4-aminopiperidine (8.0 g; 0.04 moles) in anhydrous tetrahydrofuran (50 ml) was added, the temperature was maintained at -5° to -10° C. for 1 hour and then 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 an oil which was treated with the stoichiometric amount of fumaric acid in boiling absolute ethanol. N-[1-(2-Tetrahydrofurylmethyl)-piperid-4-yl]-2-ethoxy-4-amino-5-chlorobenzamide hydrogen fumarate (10.6 g) was thus obtained, m.p. 199°-201° C. (d).

Workup

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

Sources & evidence

ORD record
ord-187fc3d91abd4aa0abfb273f6f36c019
Source dataset
uspto-grants-1988_09
Patent number
US04772618

Reaction notes

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