Pyrrolidine → HCID 898715, compound

HRID 1386991Notes

Reaction equation

HRID 1386991 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C:8]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:10])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 99777p-Bromocinnamic acid

Product 1

HCID 898715HCID 898715, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.0 g (22.0 mmol) of 4-bromocinnamic acid, 6 mL of oxalyl chloride and 3 drops of DMF in 40 mL of CH2Cl2 was heated to gentle reflux until gas evolution ceased. The volatiles were removed in vacuo and the residue was taken up in 50 mL of CH2Cl2. Pyrrolidine (10 mL; 120 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was evaporated in vacuo and chromatographed to afford 5.36 g (19.1 mmol; 87%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto gentle reflux until gas evolution
  3. customThe volatiles were removed in vacuo
  4. customThe reaction mixture was evaporated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-483ec6c615d94aa5a5e410972f1a0b51
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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