Sodium Hydroxide → HCID 14053215, compound

HRID 1252503Notes

Reaction equation

HRID 1252503 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.Cl.Cl[CH2:13][C:14]1[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:17]([CH3:26])=[CH:16][N:15]=1.[OH-].[Na+]>C(O)C>[CH3:26][C:17]1[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:19][C:14]([CH2:13][S:1][C:2]2[NH:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 140532121H-indole-2-thiolHCID 14053214HCID 14053214, compound

Product 1

HCID 14053215HCID 14053215, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-mercaptoindole (1.34 g, 8.98 mmol) and 2-chloromethyl-5-methyl-4-piperidinopyridine hydrochloride (2.35 g, 9.00 mmol) in ethanol (90 ml) was added a 2N aqueous sodium hydroxide solution (9.0 ml) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. After the removal of the organic solvent by evaporation under a reduced pressure, a saturated sodium chloride solution was added to the residue and the mixture was extracted with chloroform. The chloroform layer separated was dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was purified by a silica gel column chromatography [eluent: chloroform and then chloroform-methanol (50:1)] whereby to yield the titled compound (2.51 g) as a crystalline substance.

Workup

  1. temperaturecooling
  2. customAfter the removal of the organic solvent
  3. customby evaporation under a reduced pressure
  4. additiona saturated sodium chloride solution was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. customThe chloroform layer separated
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by a silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-f572d70d3e4b483d847b8083d5019f7b
Source dataset
uspto-grants-1988_05
Patent number
US04743609

Reaction notes

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