Water → N-{2-[2-(1-Methylpiperidin-2-yl)ethyl]phenyl}pyridine-2-carboxamide

HRID 1659265Notes

Reaction equation

HRID 1659265 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH3:12].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](OCC)=[O:24].[H-].[Na+].O>CS(C)=O>[CH3:12][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH2:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[NH:1][C:23](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 17307Ethyl 2-pyridinecarboxylateHCID 24758Sodium hydrideHCID 110852822-(2-Aminophenethyl)-1-methylpiperidine

Product 1

HCID 20560098N-{2-[2-(1-Methylpiperidin-2-yl)ethyl]phenyl}pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(o-aminophenethyl)-1-methylpiperidine (8.0 g., 0.037 mole) and ethyl picolinate (5.5 g., 0.037 mole) in DMSO (20 ml.) is treated with NaH (57%) in oil (1.6 g., 0.037 mole) with intermittent cooling to moderate the resulting vigorous reaction. After 2 hr., the mixture is poured into 150 ml. of H2O and the product isolated according to the procedure of Example 25. Crystallization from isopropyl ether affords 5.9 (50%) of analytically pure 2'-[2-(1-methyl-2-piperidyl)ethyl]picolinanilide, m.p. 65.5°-67° C. (corr.).

Workup

  1. temperaturecooling
  2. customthe resulting vigorous reaction
  3. addition, the mixture is poured into 150 ml
  4. customCrystallization from isopropyl ether

Sources & evidence

ORD record
ord-26b4636c0e4d4dd7893788acbe0ec7ba
Source dataset
uspto-grants-1981_12
Patent number
USRE030812

Reaction notes

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