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

HRID 1034426Notes

Reaction equation

HRID 1034426 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 199366514-[(2,2-Diethoxyethyl)thio]-1-(phenylmethyl)piperidine

Product 1

HCID 199366495-chloro-3-[[1-(phenylmethyl)piperidin-4-yl]thio]-1H-indole hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Chlorophenylhydrazine hydrochloride (1 g) and 4-[(2,2-diethoxyethyl)thio]-1-(phenylmethyl)piperidine (prepared in Example 12) 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

  1. customis formed
  2. filtrationthe precipitate is filtered off
  3. extractionextracted with ether
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f364fcd629f84f3a8aa931cc3f223f8e
Source dataset
uspto-grants-1994_05
Patent number
US05317025

Reaction notes

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