Triethylamine → HCID 70447826, compound

HRID 2290589Notes

Reaction equation

HRID 2290589 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:14][CH3:15])[CH:9]=[C:10]([C:11]([OH:13])=O)[C:4]=2[O:3]1.C(N(CC)CC)C.C([Cl:28])(=O)OCC.[CH2:29]([N:31]1[CH2:35][CH2:34][CH2:33][CH:32]1[CH2:36][NH2:37])[CH3:30]>CC(C)=O>[ClH:28].[CH2:29]([N:31]1[CH2:35][CH2:34][CH2:33][CH:32]1[CH2:36][NH:37][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][CH3:15])[CH:9]=1)=[O:13])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 14709032HCID 14709032, compound

Product 1

HCID 70447826HCID 70447826, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

2-Methyl-5-methylthio-2,3-dihydrobenzofuran-7-carboxylic acid, 4.6 g, is dissolved in 50 ml of acetone, 6.9 ml of triethylamine is added and the whole is stirred. Under cooling at 10° C. 2.7 g of ethyl chlorocarbonate is added dropwise for 3-5 minutes. After stirring at room temperature for 30 minutes, 3.4 g of 1-ethyl-2-aminomethylpyrrolidine is added and the reactant is stirred at room temperature for 20 minutes and allowed to stand for 15 hours. Then, excess triethylamine and acetone are distilled off under reduced pressure. To the resulting residue is added 50 ml of water, and the solution is extracted three times with ethyl acetate. The ethyl acetate extract layer is washed with sodium bicarbonate saturated aqueous solution, water and sodium chloride saturated water in this sequence, dried and blown into by hydrochloric acid gas. Excess hydrochloric acid gas and ethyl acetate are distilled off under reduced pressure. To the residue are added 60 ml of ethyl acetate and 30 ml of ether to cause crystallization at 0° C. Deposited crude crystals are recrystallized from a mixed solvent of ethyl acetate/isopropanol (100/7) to give crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-methylthio-2,3-dihydrobenzofuran-7-carboxamide hydrochloride, m.p. 145°-150° C.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. stirringthe reactant is stirred at room temperature for 20 minutes
  3. distillationThen, excess triethylamine and acetone are distilled off under reduced pressure
  4. additionTo the resulting residue is added 50 ml of water
  5. extractionthe solution is extracted three times with ethyl acetate
  6. extractionThe ethyl acetate extract layer
  7. washis washed with sodium bicarbonate saturated aqueous solution, water and sodium chloride saturated water in this sequence
  8. customdried
  9. distillationExcess hydrochloric acid gas and ethyl acetate are distilled off under reduced pressure
  10. additionTo the residue are added 60 ml of ethyl acetate and 30 ml of ether
  11. customcrystallization at 0° C
  12. customDeposited crude crystals are recrystallized from a mixed solvent of ethyl acetate/isopropanol (100/7)

Sources & evidence

ORD record
ord-d5595fbc2ad04647bec5fa617294c0e6
Source dataset
uspto-grants-1986_10
Patent number
US04617314

Reaction notes

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