Dimethylformamide → Methyl 4-(pyrrolidin-1-ylmethyl)benzoate

HRID 1386976Notes

Reaction equation

HRID 1386976 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([OH:3])=[O:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[CH3:17]N(C=O)C>>[N:12]1([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([C:1]([O:3][CH3:17])=[O:2])=[CH:5][CH:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 225994-(Bromomethyl)benzoic acidHCID 31268Pyrrolidine

Product 1

HCID 756589Methyl 4-(pyrrolidin-1-ylmethyl)benzoate

Procedure

A solution of 6.20 mL (44.5 mmol) of TEA and 4.70 g (21.8 mmol) of 4-carboxybenzyl bromide in 50 mL of DMF was treated with 2.10 mL (25.2 mmol) of pyrrolidine at 50° C. for 3 h. The reaction mixture was cooled, evaporated in vacuo, and the residue was taken up in 50 mL of MeOH. The solution was treated with a rapid stream of HCl (g) for 15 min, the reaction vessel was sealed and the reaction stirred at ambient temperature for 16 h. Evaporation of the solvent afforded 2.56 g of an oil which was purified by radial chromatography (SiO2; 80:18:2 hexanes-THF-TEA) to afford 2.30 g (10.5 mmol; 48%) of the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in vacuo
  3. additionThe solution was treated with a rapid stream of HCl (g) for 15 min
  4. customthe reaction vessel was sealed
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8d22133b725b47b4993f1fbfe7e723ed
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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