Methyl Isocyanate → HCID 9801311, compound

HRID 1274447Notes

Reaction equation

HRID 1274447 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12]4([CH2:25][CH2:26][C:5]=3[C:4]=2[CH:3]=1)[CH2:17][CH2:16][N:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:14][CH2:13]4.[CH3:27][N:28]=[C:29]=[O:30]>ClCCl.[Cu]Cl>[CH3:11][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([O:1][C:29]([NH:28][CH3:27])=[O:30])=[CH:3][C:4]=2[C:5]2[CH2:26][CH2:25][C:12]3([CH2:13][CH2:14][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:16][CH2:17]3)[C:6]1=2

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 15461539HCID 15461539, compound

Product 1

HCID 9801311HCID 9801311, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dihydro-7-hydroxy-4-methyl-1'-phenylmethylspiro[cyclopent[b]indole-3(2H), 4'-piperidine] (0.25 g) and copper (I) chloride (0.01 g) in dichloromethane (10 ml) was added methyl isocyanate (0.04 g), under nitrogen, with stirring. The reaction mixture was stirred for 24 hrs. The mixture was flash chromatographed (neutral alumina) and eluted with 25% ethyl acetate/dichloromethane. The appropriate fractions were collected and concentrated to give 0.2 g (69%) of product, mp 189-190° C.

Workup

  1. stirringThe reaction mixture was stirred for 24 hrs
  2. customchromatographed (neutral alumina)
  3. washeluted with 25% ethyl acetate/dichloromethane
  4. customThe appropriate fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0712b976b2e44a0a1494fc85c914192
Source dataset
uspto-grants-2000_12
Patent number
US06156901

Reaction notes

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