Methyl Isocyanate → HCID 11996163, compound

HRID 2102684Notes

Reaction equation

HRID 2102684 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N:26]([CH3:29])=[C:27]=[O:28]>C(Cl)(Cl)Cl>[CH3:29][NH:26][C:27]([N:15]1[CH2:16][CH2:17][CH:12]([C:6]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:13][CH2:14]1)=[O:28]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 57803074HCID 57803074, compound

Product 1

HCID 11996163HCID 11996163, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-4-yl-1,3-dihydro-indol-2-one (30 mg, 0.08 mmol) (from Example 15a supra) in chloroform (2 mL) was added isocyanatomethane (5.4 mg, 0.096 mmol) (Chem. Service). The mixture was stirred at room temperature for 16 hours. The solvent was evaporated and resulting material was recrystallized from dichloromethane-hexanes to give rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid methylamide as a white solid. (Yield 5 mg, 14.5%).

Workup

  1. customThe solvent was evaporated
  2. customresulting material
  3. customwas recrystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-3b6335e638a841cc92882450bd13c12c
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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