Pyrrolidine → HCID 13189987, compound

HRID 2418273Notes

Reaction equation

HRID 2418273 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([CH3:21])([CH:18]=[CH:19][CH3:20])[CH:16]=O>C(O)=O>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([CH3:21])([CH2:18][CH:19]=[CH2:20])[CH2:16][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 57255885HCID 57255885, compound

Product 1

HCID 13189987HCID 13189987, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

149 g of formic acid were added dropwise to 45.8 g of pyrrolidine, while cooling with ice. 181 g of 3-(2,4-dichlorophenyl)-2-methyl-2-propen-1-ylpropionaldehyde were then added, after which the mixture was heated at 100° C. for 12 hours and then evaporated down under reduced pressure. The residue was made alkaline with 25% strength NaOH and extracted with ether, and the organic phase was dried over KOH and evaporated down. Distillation of the residue gave 95 g of (X) of boiling point 130°-138° C./0.1 mbar.

Workup

  1. temperaturewhile cooling with ice
  2. customevaporated down under reduced pressure
  3. extractionextracted with ether
  4. dry with materialthe organic phase was dried over KOH
  5. customevaporated down
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-d92ea961c8484b59bce719f353d61f7f
Source dataset
uspto-grants-1984_09
Patent number
US04472412

Reaction notes

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