m-Tolyl isocyanate → 9-benzyl-2-(3-methylphenyl)carbamyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

HRID 1106919Notes

Reaction equation

HRID 1106919 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][NH:19][CH2:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1>O1CCOCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][N:19]([C:29](=[O:30])[NH:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[CH:23]=3)[CH2:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 5986499-Benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

Product 1

HCID 187881639-benzyl-2-(3-methylphenyl)carbamyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 9-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole(2.66 g, 10.1 mmol) and 3-methylphenylisocyanate (1.42 ml, 11.0 mmol) was stirred in dioxan (40 ml) at room temperature for 4 hours. Evaporation of the solvent and chromatography on silica gel with ethyl acetate-hexane (2:3) as eluant gave the product. (3.04 g, 76%).

Workup

  1. customEvaporation of the solvent and chromatography on silica gel with ethyl acetate-hexane (2:3) as eluant
  2. customgave the product

Sources & evidence

ORD record
ord-87870b41bc6241bebdcb0496739da24d
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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