Dichloromethane → HCID 12804798, compound

HRID 1106060Notes

Reaction equation

HRID 1106060 reaction equation
Cl.[C:2]1([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]2[CH2:19][CH2:18][NH:17][CH2:16]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:20].[Na+].[CH2:22](Cl)Cl>CCOCC>[CH:22]([N:17]1[CH2:18][CH2:19][CH:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:16]1)=[O:20]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 12804797HCID 12804797, compound

Product 1

HCID 12804798HCID 12804798, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.42 g of 3-(α-phenyl-2-tolyl)pyrrolidine hydrochloride of Example 58 in 50 ml of CH2Cl2 is stirred with an excess of 5% NaOH. The organic phase is separated, washed with water, dried (Na2SO4), and evaporated to an oil. This oil is dissolved in 50 ml of ethyl formate and refluxed for 18 hours. The solvent is removed under reduced pressure to give an oil, which is dissolved in 25 ml of ether, and after cooling 16 hours the product is collected by filtration to provide 1-formyl-3-(α-phenyl-2-tolyl)pyrrolidine, mp 70°-71° C.

Workup

  1. customThe organic phase is separated
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated to an oil
  5. dissolutionThis oil is dissolved in 50 ml of ethyl formate
  6. temperaturerefluxed for 18 hours
  7. customThe solvent is removed under reduced pressure
  8. customto give an oil, which
  9. temperatureafter cooling 16 hours the product
  10. filtrationis collected by filtration

Sources & evidence

ORD record
ord-4473d520ca8c42baa22d55f7727e6c69
Source dataset
uspto-grants-1982_01
Patent number
US04311703

Reaction notes

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