Methyl Isocyanate → HCID 22411430, compound

HRID 439396Notes

Reaction equation

HRID 439396 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[OH:10])[CH:3]=[CH:2]1.CCCCCCC=CCCC.[CH3:22][N:23]=[C:24]=[O:25].CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[CH3:22][NH:23][C:24](=[O:25])[O:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2

Participants

6

Reactant 4

HCID 12228Methyl IsocyanateHCID 136496Undec-4-eneHCID 27376517-HydroxyindoleHCID 21226206Ethyl acetate hexane

Product 1

HCID 22411430HCID 22411430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(N-Cyclopropyl)amino-4-methyl-1,2,3,4-tetrahydrocyclopent b!indol-7-ol (2.2 g) was dissolved in CH2Cl2 (200 ml) with 1,8-diazabicyclo 5.4.0!undec-7-ene (DBU; 0.21 g) and the solution was cooled to 0° C. A solution of methyl isocyanate (0.52 g in 30 ml CH2Cl2) was added slowly to the cooled solution and the reaction was monitored by thin layer chromatography (silica gel, 1:1 hexane/ethyl acetate). After warming to room temperature, the mixture was washed successively with water (2×100 ml), brine (1×100 ml) and again with water (1×100 ml). The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The crude material was recrystallized from acetonitrile. 3-(N-Cyclo-propyl)amino-4-methyl-1,2,3,4-tetrahydrocyclopent b!indol-7-yl methylcarbamate was isolated as light yellow/white plates (1.0 g).

Workup

  1. washthe mixture was washed successively with water (2×100 ml), brine (1×100 ml) and again with water (1×100 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe crude material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-73048c512ac84c2a872ec78174d9a217
Source dataset
uspto-grants-1996_05
Patent number
US05514700

Reaction notes

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