N-(3-Aminopropyl)morpholine → HCID 67422167, compound

HRID 2219427Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[C:6]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][O:11][C:12]=2[CH3:13])[N:7]=1.[NH2:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CN(C=O)C>[CH3:13][C:12]1[O:11][N:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]=1[C:6]1[N:7]=[C:3]([CH2:2][NH:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[N:4]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[2-chloromethyl-1-(4-nitro-phenyl)-1H-imidazol-4-yl]-5-methyl-3-phenyl-isoxazole (50 mg, 0.13 mmol) in DMF (2 mL) was added 4-(3-aminopropyl)morpholine (36.5 mg, 0.25 mmol) and KI (4.2 mg, 0.03 mmol) and the resulting mixture heated at 80° C. for 2 h. After cooling to room temperature, the mixture was then poured onto water and extracted with ethyl acetate. The combined organic layers were then washed with brine and water and then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 80:20) afforded the title compound (47 mg, 74%) which was obtained as a yellow gum. MS: m/e=503.4 [M+H]+.

Workup

temperatureAfter cooling to room temperature
additionthe mixture was then poured onto water
extractionextracted with ethyl acetate
washThe combined organic layers were then washed with brine and water
dry with materialdried over sodium sulphate
customevaporated
customPurification by chromatography (SiO2, dichloromethane:methanol=100:0 to 80:20)

Sources & evidence

ORD record: ord-acf1406c542142fa9d146544ae77c795
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414061B2

Reaction notes

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