Water → HCID 22643430, compound

HRID 2414782Notes

Reaction equation

HRID 2414782 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH:12]([CH3:24])[CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C.O>C(#N)C>[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]=1[S:1][CH:12]([CH3:24])[CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 226434181-(4-Bromovaleroyl)-4-methylpiperidineHCID 178527775HCID 178527775, compound

Product 1

HCID 22643430HCID 22643430, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.15 g of 2-mercaptobenzimidazole and 0.26 g of 1-(4-bromovaleroyl)-4-methylpiperidin were suspended in acetonitrile, and the suspension was added with 0.17 ml of triethylamine and refluxed for 7 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:methylene chloride=1:10) to obtain 0.07 g of the title compound as oil (yield: 21%).

Workup

  1. temperaturerefluxed for 7 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol:methylene chloride=1:10)

Sources & evidence

ORD record
ord-b91d2aeead8044b499cc2c21461ad4a6
Source dataset
uspto-grants-2004_11
Patent number
US06815455B1

Reaction notes

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