3-(Dimethylamino)propyl chloride hydrochloride → 3-(3-[N,N-Dimethylamino]propylthio)-1-phenylindole hydrochloride

HRID 637650

Reaction equation

HRID 637650 reaction equation
I.[C:2]1([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([S:17][C:18](=N)N)=[CH:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25]C[Cl:27]>[OH-].[Na+].Cl>[ClH:27].[CH3:22][N:23]([CH2:24][CH2:25][CH2:18][S:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)[CH3:28]

Participants

5

Reactant 2

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 202556982-(1-Phenylindol-3-yl)-2-thioisourea hydroiodide

Product 1

HCID 202557073-(3-[N,N-Dimethylamino]propylthio)-1-phenylindole hydrochlorideYield 46%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the hydroidide salt from part (A) (27.0 g; 0.07M) in 2N aqueous sodium hydroxide (300.0 ml) was stirred under nitrogen and heated to reflux. After 10 minutes the mixture was cooled to 90° and solid 3-[dimethylamino]-propyl chloride hydrochloride (21.6 g; 0.14M) was added in small portions. A vigorous exothermic reaction occcurred and the solid dissolved. The solution was allowed to cool and was stirred at 20° for a further 17 hours. The resulting two-phase mixture was extracted with methylene chloride (3×100 ml.), and the combined organic extracts were washed with water (2×50 ml), dried (magnesium sulphate) and evaporated to give a viscous pale green oil. This was dissolved in 3.5N methanolic hydrogen chloride (50 ml.), evaporated and the residue was crystallised from acetonitrile (1200 ml.) to give the title compound as colourless leaflets, weight 11.3 g, m.p. 203°-7° (46.0% yield).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 10 minutes the mixture was cooled to 90°
  3. customA vigorous exothermic reaction
  4. dissolutionthe solid dissolved
  5. temperatureto cool
  6. stirringwas stirred at 20° for a further 17 hours
  7. extractionThe resulting two-phase mixture was extracted with methylene chloride (3×100 ml.)
  8. washthe combined organic extracts were washed with water (2×50 ml)
  9. dry with materialdried (magnesium sulphate)
  10. customevaporated
  11. customto give a viscous pale green oil
  12. customevaporated
  13. customthe residue was crystallised from acetonitrile (1200 ml.)

Sources & evidence

ORD record
ord-6694d873829d4d669d5a5ba4bb56faa7
Source dataset
uspto-grants-1985_12
Patent number
US04558048

Linked notes

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