Hydrochloric Acid → 2,5-Dimethyl-3-[[1-(phenylmethyl)piperidin-4-yl]thio]-1H-indole hydrochloride

HRID 1034425

Reaction equation

HRID 1034425 reaction equation
[ClH:1].[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.O=[C:12]([CH3:28])[CH2:13][S:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.Cl>C(O)(C)C>[ClH:1].[CH3:28][C:12]1[NH:8][C:5]2[C:6]([C:13]=1[S:14][CH:15]1[CH2:16][CH2:17][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:19][CH2:20]1)=[CH:7][C:2]([CH3:10])=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 152292804-[(2-Oxopropyl)thio]-1-(phenylmethyl)piperidine

Product 1

HCID 199366132,5-Dimethyl-3-[[1-(phenylmethyl)piperidin-4-yl]thio]-1H-indole hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Paratolylhydrazine hydrochloride (20 g) is added to a solution of 4-[(2-oxopropyl)thio]-1-(phenylmethyl)piperidine (33.2 g), prepared in Example 8, in isopropanol (150 ml) under nitrogen. After 30 minutes, the solution is cooled to 0° C. and saturated with gaseous hydrogen chloride. After 4 hours at room temperature, the precipitate formed is filtered off, washed with water and then taken up in hot ethanol. After cooling, the white crystals of 2,5-dimethyl-3-[[1-(phenylmethyl) piperidin-4-yl]thio]-1H-indole hydrochloride (28.3 g) are filtered off.

Workup

  1. waitAfter 4 hours at room temperature
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. temperatureAfter cooling
  6. filtrationthe white crystals of 2,5-dimethyl-3-[[1-(phenylmethyl) piperidin-4-yl]thio]-1H-indole hydrochloride (28.3 g) are filtered off

Sources & evidence

ORD record
ord-1632fcca9ac24ab6ba0dc8cb086fa028
Source dataset
uspto-grants-1994_05
Patent number
US05317025

Linked notes

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