Water → HCID 70448321, compound

HRID 2290590Notes

Reaction equation

HRID 2290590 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=[C:10]([C:11]([OH:13])=O)[C:4]=2[O:3]1.C([Cl:23])(=O)OCC.[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH2:32])[CH3:25].O>CN(C)C=O.CC(C)=O.C(N(CC)CC)C>[ClH:23].[CH2:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH:32][C:11]([C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[CH:7]=[C:8]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:9]=1)=[O:13])[CH3:25]

Participants

8

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 14709031HCID 14709031, compound

Product 1

HCID 70448321HCID 70448321, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-Methyl-5-methylsulfonyl-2,3-dihydrobenzofuran-7-carboxylic acid, 5.0 g, is dissolved in a mixed solvent of 40 ml of dimethylformamide and 20 ml of acetone, 6.5 ml of triethylamine is added, and the whole is stirred. At room temperature, 2.3 g of ethyl chlorocarbonate is added and the solution is stirred for one hour. Thereafter, 3.0 g of 1-ethyl-2-aminomethylpyrrolidine is added, and the reactant is stirred for one and a half hours and allowed to stand for 15 hours. After excess triethylamine and acetone are distilled off under reduced pressure, the residue obtained is poured into 300-400 ml of water and extracted three times with ethyl acetate. The extract layer is washed with aqueous sodium bicarbonate solution and water and dried. The ethyl acetate is distilled off under diminished pressure and the resulting residue is again dissolved in chloroform and hydrochloric acid is blown into the solution. Excess hydrochloric acid gas and chloroform are distilled off under reduced pressure and the resulting residue is dissolved into 35-40 ml of isopropanol and filtered. To the filtrate solution is added 110-120 ml of ethyl acetate and the system is cooled with ice to give crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-methylsulfonyl-2,3-dihydrobenzofuran-7-carboxamide hydrochloride, m.p. 186°-189° C.

Workup

  1. additionis added
  2. stirringthe solution is stirred for one hour
  3. stirringthe reactant is stirred for one and a half hours
  4. distillationAfter excess triethylamine and acetone are distilled off under reduced pressure
  5. customthe residue obtained
  6. extractionextracted three times with ethyl acetate
  7. washThe extract layer is washed with aqueous sodium bicarbonate solution and water
  8. customdried
  9. distillationThe ethyl acetate is distilled off under diminished pressure
  10. dissolutionthe resulting residue is again dissolved in chloroform
  11. distillationExcess hydrochloric acid gas and chloroform are distilled off under reduced pressure
  12. dissolutionthe resulting residue is dissolved into 35-40 ml of isopropanol
  13. filtrationfiltered
  14. additionTo the filtrate solution is added 110-120 ml of ethyl acetate
  15. temperaturethe system is cooled with ice

Sources & evidence

ORD record
ord-20b6aec1abe743cbadd5f37b4e2fe69d
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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