Morpholine → HCID 14129810, compound

HRID 1252081Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:26])[CH2:24][CH2:25][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1

Participants

Reactant 2

HCID 8083Morpholine

HCID 20140938HCID 20140938, compound

Product 1

HCID 14129810HCID 14129810, compound

Conditions

Temperature: 105 °C

Procedure

A mixture of 4-[4-(3-indolyl)piperidinomethyl]-2-acryloylaminothiazole (360 mg) and morpholine (870 mg) was heated at 105° C. After the reaction finished, excess morpholine was distilled off, and the residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1 V/V) to give 4-[4-(3-indolyl)piperidinomethyl]2-(3-morpholinopropionylamino)thiazole, which was treated with an ethanol solution of hydrogen chloride to give dihydrochloride thereof.

Workup

distillationexcess morpholine was distilled off
customthe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1 V/V)

Sources & evidence

ORD record: ord-e88b3e049b364a768627880c17afe782
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04742057

Reaction notes

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