Hydrochloric Acid → 5-chloro-3-[[1-(phenylmethyl)piperidin-4-yl]thio]-1H-indole hydrochloride

HRID 36885

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

4-Chlorophenylhydrazine hydrochloride (1 g) and 4-[(2,2-diethoxyethyl)thio]-1-(phenylmethyl)piperidine (1.8 g, prepared in Example 13) in isopropanol (20 ml) are stirred at room temperature under nitrogen until a solution is formed. After cooling to 0° C., the solution is saturated with gaseous hydrogen chloride. After 4 hours, the precipitate is filtered off, taken up in sodium hydroxide and extracted with ether and then with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated. The residual oil is taken up in a solution of hydrogen chloride in ether to give 5-chloro-3-[[1-(phenylmethyl)piperidin-4-yl]thio]-1H-indole hydrochloride (1.4 g).

Workup

customis formed
filtrationthe precipitate is filtered off
extractionextracted with ether
dry with materialThe combined organic phases are dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-b3d6b48e80694b83ad26879e1d473efd
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05418242

Linked notes

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