Indole → [2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine

HRID 16615

Reaction equation

HRID 16615 reaction equation
CN1[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.ClC(Cl)(Cl)C(O)=O.[OH-].[Na+].C(OCC)(=O)C.CO.[CH2:37]([N:39](CC)CC)C>C1COCC1.C(OCC)(=O)C>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH2:6][CH2:37][NH2:39])=[CH:12]1

Participants

8

Reactant 5

HCID 798IndoleHCID 6421Trichloroacetic AcidHCID 14798Sodium HydroxideHCID 124288082-Methyl-2,3-dihydro-benzo[d]isothiazoleHCID 21980445Ethyl acetate methanol triethylamine

Product 1

HCID 15979848[2-(1H-Indol-3-ylsulfanyl)benzyl]methylamineYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-2,3-dihydro-benzoisothiazole (VI) (Hoffmann, R. W.; Goldman, S. Chem. Ber. 111, 1978, 2716-2725) (75 mg, 0.50 mmol) was dissolved in THF (1 mL) and added to indole (V) (140 mg, 0.60 mmol) under Ar. Tricloroacetic acid (90 mg, 0.55 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. 2 mL 1N NaOH (aq) was added. Extraction with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent: ethyl acetate then ethyl acetate/methanol/triethylamine) gave 88 mg [2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine (67% yield).

Workup

  1. extractionExtraction
  2. customwith ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-d61e73bbb6e7434bbed276ddafd1091b
Source dataset
uspto-grants-2010_06
Patent number
US07737170B2

Linked notes

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