Triethylamine → 1,3-Dibenzylpyrrolidine-3-carboxylic acid amide

HRID 729448Notes

Reaction equation

HRID 729448 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:13](O)=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:25]1C=CN=C1)=O.C(N(CC)CC)C.[NH4+].[OH-]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:13]([NH2:25])=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 219793511,3-Dibenzylpyrrolidine-3-carboxylic acid

Product 1

HCID 219790091,3-Dibenzylpyrrolidine-3-carboxylic acid amideYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,3-dibenzylpyrrolidine-3-carboxylic acid (Example A28, 4.0 g, 13.5 mmol), 1,1′-carbonyldiimidazole (2.42 g, 14.9 mmol), and triethylamine (2.08 mL, 14.9 mmol) in tetrahydrofuran (100 mL) is heated at reflux for 1.5 hours. The solution is cooled, poured into NH4OH (300 mL), and stirred for 18 hours. The mixture is extracted with chloroform, the organic layer is washed with water, dried, and concentrated to afford 4.13 g of the title compound as an oil; MS EI+: m/z 295 (MH+).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe solution is cooled
  4. extractionThe mixture is extracted with chloroform
  5. washthe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-24b354f32447486eba6b1764f5f0006f
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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