1,1'-Carbonyldiimidazole → HCID 10465394, compound

HRID 1646751Notes

Reaction equation

HRID 1646751 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:11][CH2:12][NH2:13].[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>O1CCCC1>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:14](=[O:15])[NH:13][CH2:12][CH2:11][C:3]=12

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118195262-(3-methyl-1H-indol-2-yl)ethan-1-amine

Product 1

HCID 10465394HCID 10465394, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(3-methylindol-2-yl)ethylamine (1.74 g) in tetrahydrofuran (200 ml) at room temperature was added 1,1'-carbonyldiimidazole (1.6 g) in small portions. After one hour of stirring, the reaction mixture was evaporated in vacuo. The residue was dissolved in toluene and the solution was evaporated in vacuo. The oil obtained was heated at 100° C. for 40 minutes and then cooled. Purification of the residue with silica gel column chromatography (chloroform) gave 3,4-dihydro-5-methylpyrimido[1,6-a]indol-1(2H)-one (0.8 g).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in toluene
  3. customthe solution was evaporated in vacuo
  4. customThe oil obtained
  5. temperaturecooled
  6. customPurification of the residue with silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-9f6f8476120f4adb95651dbc5db63a48
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

Loading…