Morpholine → N-methoxy-N-methyl-2-morpholin-4-yl-isonicotinamide

HRID 419196Notes

Reaction equation

HRID 419196 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C(OCC)(=O)C.[Pd].C1(=O)C2C(=CC=CC=2)C(=O)C=C1>[CH3:10][O:9][N:7]([CH3:8])[C:5](=[O:6])[C:4]1[CH:11]=[CH:12][N:13]=[C:2]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 185068942-Chloro-N-methoxy-N-methylisonicotinamideHCID 23676156Sodium t-butoxide

Product 1

HCID 57942148N-methoxy-N-methyl-2-morpholin-4-yl-isonicotinamide

Reagents, catalysts & solvents 3

HCID 866107791,4-Naphthoquinone palladium(0)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-N-methoxy-N-methyl-isonicotinamide (800 mg, 4 mmol), morpholine (452 mg, 5.2 mmol), sodium tert-butoxide (500 mg, 5.2 mmol), 1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidene(1,4-naphthoquinone palladium(0) dimer in dioxane (4 mL) was stirred at 80° C. overnight. The mixture was diluted with ethyl acetate, washed with water and purified by flash column to give N-methoxy-N-methyl-2-morpholin-4-yl-isonicotinamide.

Workup

  1. washwashed with water
  2. custompurified by flash column

Sources & evidence

ORD record
ord-000824a19cd44d92ad5c1154a859c18f
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

Loading…