Diisopropylethylamine → HCID 67187228, compound

HRID 551805Notes

Reaction equation

HRID 551805 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1.C(N(C(C)C)CC)(C)C.Cl[C:34](Cl)([O:36][C:37](=O)[O:38]C(Cl)(Cl)Cl)Cl.C(=O)([O-])O.[Na+]>ClCCl.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:37]([O:36][CH3:34])=[O:38])[CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 67188496HCID 67188496, compound

Product 1

HCID 67187228HCID 67187228, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.25 g of 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline, 8.1 ml of dichloromethane and 0.3 ml of diisopropylethylamine are placed in a 50 ml round-bottomed flask under a nitrogen atmosphere. 0.12 g of triphosgene is added at 0° C. and then the reaction mixture is left stirring at ambient temperature for three hours. 0.5 ml of diisopropylethylamine and 0.33 ml of methanol are subsequently added and the reaction mixture is stirred for twenty-four hours. A saturated aqueous sodium hydrogencarbonate solution and dichloromethane are added. The aqueous phase is extracted three times with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution and dried over sodium sulfate and then the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture. 0.112 g of methyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydroquinoxaline-1(2H)-carboxylate is obtained.

Workup

  1. waitthe reaction mixture is left
  2. stirringthe reaction mixture is stirred for twenty-four hours
  3. extractionThe aqueous phase is extracted three times with dichloromethane
  4. washwashed with water and with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture

Sources & evidence

ORD record
ord-bb200ce2fc1344cf9b19470e82388d9c
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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