Pyrrolidine → HCID 68594952, compound

HRID 1516621Notes

Reaction equation

HRID 1516621 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)#[N:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[ClH:17].O1CCOCC1>C(O)C>[ClH:17].[ClH:17].[NH:2]=[C:1]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 31268Pyrrolidine2×HCID 27611086-Cyanopyridine-3-carboxylic acidHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 68594952HCID 68594952, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Cyanonicotinic acid (4.15 g, 28.0 mmol) was dissolved in anhydrous ethanol (3.2 ml) and 4N hydrochloric acid/1,4-dioxane (30 ml), and the mixture was stirred in a closed system at room temperature for two nights. The solvent was evaporated under reduced pressure, and the obtained residue was suspended in anhydrous ethanol (90 ml). Pyrrolidine (2.34 ml, 28.0 mmol) was added thereto, and the mixture was stirred at room temperature for 3 days. Pyrrolidine (3.51 ml, 42.0 mmol) was added again, and the mixture was stirred for 2.5 hours. The solvent was evaporated under reduced pressure, and water aid ethanol were added to the obtained residue. The precipitate was removed by filtration, ethanol was evaporated under reduced pressure, and the obtained aqueous solution was lyophilized to give the title compound without purification operation.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. stirringthe mixture was stirred for 2.5 hours
  3. customThe solvent was evaporated under reduced pressure, and water aid ethanol
  4. additionwere added to the obtained residue
  5. customThe precipitate was removed by filtration, ethanol
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e6c831969b9479dba4e46ae8bed3eb2
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

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