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 1168327Notes

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

Conditions

Temperature: 92.5 °C

Procedure

A suspension of 2.93 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. MS m/e (%): 269 (M+, 100).

Workup

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

Sources & evidence

ORD record: ord-f00ed08e069b4ce9b99561bf5c265504
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624176B2

Reaction notes

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