Carbon Dioxide → 1-Benzyl-2-(3,4-dimethoxybenzylidene)pyrrolidine

HRID 1278041Notes

Reaction equation

HRID 1278041 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[C:13](C(OCC)=O)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)=O.[OH-].[Na+]>>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54504210HCID 54504210, compound

Product 1

HCID 542715801-Benzyl-2-(3,4-dimethoxybenzylidene)pyrrolidine

Procedure

Boil 31.5 g of 1-benzyl-2-(α-ethoxycarbonyl-3,4-dimethoxybenzylidene)pyrrolidine under reflux with 75 ml of conc. hydrochloric acid until carbon dioxide ceases to evolve. After cooling, alkalize the thus-prepared reaction mixture with sodium hydroxide solution. Recrystallize the formed precipitate from ethanol to obtain a yield [11.3 g (44% of theory)] of title compound (m.p. 105°).

Workup

  1. temperatureAfter cooling
  2. customRecrystallize the formed precipitate from ethanol
  3. customto obtain

Sources & evidence

ORD record
ord-433b592459bd485483b54aa24a7dc495
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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