2,2-Dimethyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide → 6-Morpholin-4-yl-4-o-tolyl-pyridin-3-ylamine

HRID 379388Notes

Reaction equation

HRID 379388 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:7]=[N:8][C:9]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=O>Cl.C(O)CC>[N:19]1([C:9]2[N:8]=[CH:7][C:6]([NH2:5])=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH:10]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 154860502,2-Dimethyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide

Product 1

HCID 154860516-Morpholin-4-yl-4-o-tolyl-pyridin-3-ylamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 10311-PropanolSolvent

Procedure

A suspension of2.93 g (8.28 mmol)2,2-dimethyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide in 80 ml 3 N hydrochloric acid solution and 5 ml 1-propanol was heated to 90-95° C. overnight. The reaction mixture was cooled to room temperature, washed with three 20 ml portions diethyl ether and filtered over celite. The filtrate was diluted with 20 ml water and was adjusted to pH 7-8 by addition of 28% sodium hydroxide solution under ice cooling. The product was extracted with four 100 ml portions of dichloromethane. The combined organic layers were washed with 50 ml brine, dried (magnesium sulfate) and evaporated to give 2.31 g (quantitative) of the title compound as a white foam.

Workup

  1. washwashed with three 20 ml portions diethyl ether
  2. filtrationfiltered over celite
  3. additionThe filtrate was diluted with 20 ml water
  4. additionwas adjusted to pH 7-8 by addition of 28% sodium hydroxide solution under ice cooling
  5. extractionThe product was extracted with four 100 ml portions of dichloromethane
  6. washThe combined organic layers were washed with 50 ml brine
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated

Sources & evidence

ORD record
ord-d285fc9b09e848f1988597ab4481417d
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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