Methyl iodide → HCID 57513876, compound

HRID 2262729Notes

Reaction equation

HRID 2262729 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:28])[CH2:12][N:13]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][C:19]4=[O:27])[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.IC.[C:31]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:28])[CH2:12][N:13]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([CH3:31])[C:19]4=[O:27])[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 57513875HCID 57513875, compound

Product 1

HCID 57513876HCID 57513876, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1′-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]spiro[indole-3,4′-piperidin]-2(1H)-one (0.136 mmol), iodomethane (0.544 mmol) and Cs2CO3 (177 mg, 0.544 mmol) in DMF (3 ml) is heated in a sealed tube at 65° C. overnight. DMF is removed in vacuo and the residue is partitioned between water (5 ml) and EtOAc (10 ml). The layers are separated and the aqueous layer is extracted with EtOAc (10 ml). The combined extracts are washed with brine (20 ml), dried over Na2SO4 and evaporated. Purification of the residue with PTLC gives the title compound as a white solid. LC-MS (M+1): 396.3.

Workup

  1. customDMF is removed in vacuo
  2. customthe residue is partitioned between water (5 ml) and EtOAc (10 ml)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 ml)
  5. washThe combined extracts are washed with brine (20 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customPurification of the residue with PTLC

Sources & evidence

ORD record
ord-3345b187e6f84e7eae3cb87769834e3c
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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