Dimethylamine → HCID 67188213, compound

HRID 551803Notes

Reaction equation

HRID 551803 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.[CH:24]([N:27]([CH:30](C)C)[CH2:28]C)(C)C.ClC(Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl.CNC>O1CCCC1.O.ClCCl>[CH3:24][N:27]([CH3:30])[C:28]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]([C:12]([N:9]2[CH2:10][CH2:11][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8]2)=[O:13])[CH2:15][CH2:16]1)=[O:36]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 67188496HCID 67188496, compound

Product 1

HCID 67188213HCID 67188213, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

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 0.5 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 one and a half hours. 0.5 ml of diisopropylethylamine and 2.03 ml of a 2N solution of dimethylamine in tetrahydrofuran are subsequently added and the reaction mixture is stirred for eighteen hours. Water is added and then the aqueous phase is extracted three times with dichloromethane. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 90/10 mixture. 0.22 g of N,N-dimethyl-4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydroquinoxaline-1(2H)-carboxamide 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. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a dichloromethane/methanol 90/10 mixture

Sources & evidence

ORD record
ord-50515dbac9e04c2388a335a2cf5e993d
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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