Water → 2-Cyclopentyl-N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-acetamide

HRID 1158692

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:14])[C:3]=1[NH2:15].[CH:16]1([CH2:21][C:22](Cl)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1.O>C(#N)C>[CH:16]1([CH2:21][C:22]([NH:15][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:5][C:4]=2[CH3:14])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 150 °C

Procedure

2,6-Dimethyl-4-morpholin-4-yl-phenylamine (0.50 g) and cyclopentylacetyl chloride (0.53 mL) were dissolved in acetonitrile (5 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Water (25 mL) was added and the product was extracted with ethyl acetate (3×25 mL). The organic phases were washed with brine (50 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 0.138 g (20%) of the title compound as an off-white solid. LC-MS-TOF (m/z) 317 (MH+); tR=1.93, (UV, ELSD) 95%, 100%. 1H NMR (500 MHz, DMSO-d6): 1.21 (m, 2H), 1.52 (m, 2H), 1.61 (m, 2H), 1.76 (m, 2H), 2.07 (s, 6H), 2.11 (m, 1H), 2.25 (d, 2H), 3.05 (dd, 4H), 3.71 (dd, 4H), 6.63 (s, 2H), 8.94 (s, 1H).

Workup

extractionthe product was extracted with ethyl acetate (3×25 mL)
washThe organic phases were washed with brine (50 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-8b9402af3722436eb2cdb0dc70b94978
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812023B2

Linked notes

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