Triethylamine → Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

HRID 1196511Notes

Reaction equation

HRID 1196511 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=1.[CH2:13]([N:15](CC)[CH2:16][CH3:17])[CH3:14].N1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:15]1([CH2:2][C:3]2[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=2)[CH2:16][CH2:17][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 14625089Methyl 2-(chloromethyl)-4-pyridinecarboxylate

Product 1

HCID 15123252Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of product of stage (iii) (1.6 g) in dry dichloromethane (50 ml) at -50° was treated with triethylamine (1.07 ml) and the mixture was stirred for 5 min. A pre-cooled solution of pyrrolidine (1.28 ml) in dry dichloromethane (30 ml) was added at -60° and the mixture was stirred at -60° to 0° for 1 h and at ambient temperature for 72 h. The mixture was poured into aqueous sodium carbonate (1M; 50 ml) and the product was extracted with dichloromethane (50 ml). The organic solution was dried and evaporated leaving an oily residue (1.7 g) which was purified by flash chromatography eluting with dichloromethane/methanol/ammonia 200:10:1 to give the title compound as an oil (0.3 g).

Workup

  1. stirringthe mixture was stirred at -60° to 0° for 1 h and at ambient temperature for 72 h
  2. extractionthe product was extracted with dichloromethane (50 ml)
  3. customThe organic solution was dried
  4. customevaporated

Sources & evidence

ORD record
ord-c292ac9679cd4d149a053af40438d7a2
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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