1-(2-Chloroethyl)pyrrolidine → HCID 23334040, compound

HRID 904293Notes

Reaction equation

HRID 904293 reaction equation
[C:1]1([C:7]2[C:8](=[O:18])[O:9][C:10]3[C:15]([C:16]=2[OH:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:19]1([CH2:24][CH2:25]Cl)[CH2:23][CH2:22][CH2:21][CH2:20]1>>[N:19]1([CH2:24][CH2:25][O:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[O:9][C:8](=[O:18])[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 54688870Coumarin, 4-hydroxy-3-phenyl-

Product 1

HCID 23334040HCID 23334040, compoundYield 46%

Procedure

In accordance with Example 1, 10 g. (0.042 mol) of 3-phenyl-4-hydroxy-coumarin are caused to react with 9.3 g. (0.055 mol) of 2-pyrrolidino-1-chlorethane. After evaporation of the methyl isobutyl ketone, the pasty residue is taken up under heat in 150 ml. of a 5% solution of sodium bicarbonate, this being followed by cooling and extraction with chloroform. The substance obtained is dried over Na2SO4 and the chloroform is evaporated under vacuum. A brown oil is obtained. Weight 6.5 g.; yield 46% (theoretical yield 14.1 g.).

Workup

  1. customto react with 9.3 g
  2. customAfter evaporation of the methyl isobutyl ketone
  3. temperatureunder heat in 150 ml
  4. temperatureby cooling
  5. extractionextraction with chloroform
  6. customThe substance obtained
  7. dry with materialis dried over Na2SO4
  8. customthe chloroform is evaporated under vacuum
  9. customA brown oil is obtained

Sources & evidence

ORD record
ord-14c628011a7142b9b5bb6c23484ac570
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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