Diisopropylethylamine → HCID 67188217, compound

HRID 551814Notes

Reaction equation

HRID 551814 reaction equation
Cl.[NH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.ClC(Cl)(O[C:29](=[O:35])OC(Cl)(Cl)Cl)Cl.[NH:37]1[CH2:41][CH2:40][CH:39]([C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)[CH2:38]1>ClCCl.O>[N:44]1[CH:45]=[CH:46][CH:47]=[C:42]([CH:39]2[CH2:40][CH2:41][N:37]([C:29]([N:2]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=4)[CH2:5][CH2:4][CH2:3]3)=[O:35])[CH2:38]2)[CH:43]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 67188214Methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate hydrochloride

Product 1

HCID 67188217HCID 67188217, compoundYield 176.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.6 g of methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate hydrochloride, 13.2 ml of dichloromethane and 2.54 ml of diisopropylethylamine are placed in a 100 ml round-bottomed flask under a nitrogen atmosphere. 0.31 g of triphosgene is added at 0° C. and then the reaction mixture is left stirring at ambient temperature for three hours. 0.39 g of 3-(pyrrolidin-3-yl)pyridine is subsequently added and the reaction mixture is stirred for eighteen hours. Water 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. 0.675 g of methyl 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoline-6-carboxylate is obtained.

Workup

  1. waitthe reaction mixture is left
  2. stirringthe reaction mixture is stirred for eighteen 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-68a4bc36a97b4427b425601bea628e16
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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