N-(4-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-yl)acetamide → 4-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-amine

HRID 1252071Notes

Reaction equation

C([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13][CH2:12]2)[N:9]=1)(=O)C>C(O)C.Cl>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13][CH2:12]2)[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Acetylamino-4-[4-(3-indolyl)piperidinomethyl]thiazole (1.2 g) in a mixture of ethanol (3 ml) and 10% hydrochloric acid (9 ml) was stirred at 80° C. for 2.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added dropwise 10% aqueous sodium hydroxide solution (12 ml) under ice-cooling. The resulting crystals were collected, washed with water, dried and recrystallized from ethanol to give 2-amino-4-[4-(3-indolyl)piperidinomethyl]thiazole (410 mg).

Workup

temperatureAfter cooling to ambient temperature
concentrationthe reaction mixture was concentrated under reduced pressure
additionTo the residue was added dropwise 10% aqueous sodium hydroxide solution (12 ml) under ice-
temperaturecooling
customThe resulting crystals were collected
washwashed with water
customdried
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-2a03d9646e914b73bf2469335d9c3bdd
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04742057

Reaction notes

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