Methyl iodide → HCID 12050334, compound

HRID 2230172Notes

Reaction equation

HRID 2230172 reaction equation
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:16][CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:33]>CN(C=O)C.C(Cl)Cl>[CH3:33][N:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:20]([CH:17]2[CH2:18][CH2:19][N:14]([C:7]3([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:15][CH2:16]2)[C:21]1=[O:29]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9821733HCID 9821733, compound

Product 1

HCID 12050334HCID 12050334, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 1-[1-(1-phenylcycloheptyl)-4-piperidyl]-1,3-dihydro-2H-1,3-benzimidazol-2-one (116 mg, 0.298 mmol) in DMF (1 ml) was added NaH (60% oil suspension, 18 mg, 0.447 mmol) at rt. After 30 min stirring at rt, iodomethane (22.3 μl, 0.358 mmol) was added to the reaction mixture at rt. After 15 min stirring at rt, the reaction mixture was diluted with CH2Cl2, washed with water and brine, dried (Na2SO4), filtered, and concentrated to give pale yellow solid, which was purified by column chromatography (silica gel:5 g, hexane/ethyl acetate:5/1-3/1) to give 83 mg (69%) of white solid.

Workup

  1. stirringAfter 15 min stirring at rt
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give pale yellow solid, which
  7. customwas purified by column chromatography (silica gel:5 g, hexane/ethyl acetate:5/1-3/1)

Sources & evidence

ORD record
ord-c701dd41538041b899781676d36b2aa9
Source dataset
uspto-grants-2002_07
Patent number
US06423725B1

Reaction notes

Loading…