Pyridine → HCID 21966957, compound

HRID 456361Notes

Reaction equation

HRID 456361 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8]C=1.[C:12]12([C:28](Cl)=[O:29])[CH2:21][C:16]3([C:22](Cl)=[O:23])[CH2:17][CH:18]([CH2:20][C:14]([C:25](Cl)=[O:26])([CH2:15]3)[CH2:13]1)[CH2:19]2>C(Cl)Cl>[N:1]1([C:28]([C:12]23[CH2:21][C:16]4([C:22]([N:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:23])[CH2:17][CH:18]([CH2:20][C:14]([C:25]([N:6]5[CH2:8][CH2:9][CH2:10][CH2:11]5)=[O:26])([CH2:15]4)[CH2:13]2)[CH2:19]3)=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31268PyrrolidineHCID 21966958HCID 21966958, compound

Product 1

HCID 21966957HCID 21966957, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 500-ml flask equipped with a stirrer, a thermometer and a dropping funnel were placed 34.5 g (485 mmol) of pyrrolidine, 38.4 g (485 mmol) of pyridine and 140 ml of methylene chloride. To the stirred mixture under ice-cooling in a nitrogen atmosphere, 31.4 g (97 mmol) of 1,3,5-adamantanetricarbonyl trichloride in 190 ml of methylene chloride was added dropwise over 1 hour. This was warmed to room temperature, was stirred for further 1 hour and was washed with water, 1 N hydrochloric acid, and 10% aqueous sodium carbonate solution, and the solvent was removed under reduced pressure, to yield 37.2 g (87 mmol) of 1,3,5-tris(1-pyrrolidinylcarbonyl)adamantane in a yield of 90%.

Workup

  1. customIn a 500-ml flask equipped with a stirrer
  2. additionwas added dropwise over 1 hour
  3. washwas washed with water, 1 N hydrochloric acid, and 10% aqueous sodium carbonate solution
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f13c8d6f5eec4384a33b4efb236d4d6e
Source dataset
uspto-grants-2007_03
Patent number
US07186454B2

Reaction notes

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