Hexane → HCID 10107502, compound

HRID 1646766Notes

Reaction equation

HRID 1646766 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH2:17][CH2:18][NH:19][C:20](N1C=CN=C1)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC>C1(C)C(C)=CC=CC=1>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]2[C:20](=[O:21])[NH:19][CH2:18][CH2:17][C:9]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8058HexaneHCID 9974791HCID 9974791, compound

Product 1

HCID 10107502HCID 10107502, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of N-[2-(3-benzylindol-2-yl)ethyl]-1-imidazolecarboxamide (2.4 g) in xylene (50 ml) was refluxed for 3 hours. After cooling, the mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (5%-methanol-chloroform) to give a crystalline product. The product was pulverized with n-hexane to give 5-benzyl-3,4-dihydropyrimido[1,6-a]indol-1(2H)-one (1.2 g).

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (5%-methanol-chloroform)
  6. customto give a crystalline product

Sources & evidence

ORD record
ord-5524f8db5b4544629266fb16fa5d9c01
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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