Methyl Isocyanate → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(3-methylureido)methylindole

HRID 1790531Notes

Reaction equation

HRID 1790531 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH2:28])[CH:25]=4)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1>C(OCC)(=O)C>[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH:28][C:3]([NH:2][CH3:1])=[O:4])[CH:25]=4)[CH:20]=[CH:19]3)[CH2:16][CH2:17]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 220380351-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline

Product 1

HCID 220381501-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(3-methylureido)methylindoleYield 67.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, methyl isocyanate (0.02 g) was added dropwise into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (0.09 g) obtained in Example 132 in ethyl acetate (10 ml) and the resultant mixture was stirred at room temperature for 1 hr. The resulting precipitate was collected by filtration, washed with ether/hexane and dried to give the title compound (0.07 g) as a white powder (yield: 67%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ether/hexane
  3. customdried

Sources & evidence

ORD record
ord-179e002ccc924b4486694817bb5e0033
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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