1,1'-Carbonyldiimidazole → 1-(1H-imidazol-1-ylcarbonyl)-1,2,3,4-tetrahydroquinoline

HRID 551789Notes

Reaction equation

HRID 551789 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].N1C2[C:17](=[CH:18][CH:19]=CC=2)[CH2:16][CH2:15][CH2:14]1>O1CCCC1>[N:8]1([C:1]([N:3]2[C:4]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:6][CH2:7]2)=[O:2])[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 109552981-(1H-imidazol-1-ylcarbonyl)-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.4 g of 1,1′-carbonyldimidazole, 125 ml of tetrahydrofuran and 9.43 ml of 1,2,3,4-tetrahydroquinoline are introduced into a 500 ml round-bottomed flask. The reaction medium is brought to reflux for 20 hours. The solvent is evaporated under reduced pressure and the residue is taken up in ethyl acetate and then washed with water. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure to result in 16.04 g of 1-(1H-imidazol-1-ylcarbonyl)-1,2,3,4-tetrahydroquinoline.

Workup

  1. temperatureto reflux for 20 hours
  2. customThe solvent is evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customto result in 16.04 g of 1-(1H-imidazol-1-ylcarbonyl)-1,2,3,4-tetrahydroquinoline

Sources & evidence

ORD record
ord-d45b2b22375c4524a2c94567a4ee9029
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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