Triethylamine → HCID 19387873, compound

HRID 1757442Notes

Reaction equation

HRID 1757442 reaction equation
[NH2:1][CH:2]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)[CH2:3][CH3:4].Cl[C:16]1[C:21]([Cl:22])=[C:20]([CH2:23][CH3:24])[N:19]=[CH:18][N:17]=1.C(N(CC)CC)C>C(O)(C)C>[Cl:22][C:21]1[C:16]([NH:1][CH:2]([CH:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6]2)[CH2:3][CH3:4])=[N:17][CH:18]=[N:19][C:20]=1[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 19387891HCID 19387891, compound

Product 1

HCID 19387873HCID 19387873, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Example P-1:1.3 g of 2-(1-aminopropyl)-1,2,3,4-tetrahydro-quinoline, 1.4 g of 4,5-dichloro-6-ethylpyrimidine and 0.85 g of triethylamine in 60 ml of absolute isopropanol are placed in a sulfonation flask at room temperature. The internal temperature of the flask is increased to 80° C. and the reaction mixture is stirred under reflux for 12 hours. The solvent is then removed under a water-jet vacuum, the residue is taken up in a mixture of 200 ml of ethyl acetate and 70 ml of water andthe mixture is shaken well. The organic phase is removed and the aqueous phase is further extracted twice, each time with 100 ml of ethyl acetate. The organic phase is dried over Na2SO4 and the solvent is removed under a water-jet vacuum. The crude product which remains can thenbe further purified by flash chromatography on silica gel (eluant: ethyl acetate/n-hexane 1:3) to yield 1.6 g of 2-[1-(5-chloro-6-ethylpyrimidin-4-ylamino)propyl]-1,2,3,4-tetrahydro-quinoline in the form of a red oil (nD50 =1.5822).

Workup

  1. customare placed in a sulfonation flask at room temperature
  2. temperatureunder reflux for 12 hours
  3. customThe solvent is then removed under a water-jet vacuum
  4. additionthe residue is taken up in a mixture of 200 ml of ethyl acetate and 70 ml of water andthe mixture
  5. stirringis shaken well
  6. customThe organic phase is removed
  7. extractionthe aqueous phase is further extracted twice
  8. dry with materialThe organic phase is dried over Na2SO4
  9. customthe solvent is removed under a water-jet vacuum
  10. customThe crude product which remains can thenbe further purified by flash chromatography on silica gel (eluant: ethyl acetate/n-hexane 1:3)

Sources & evidence

ORD record
ord-efd2418ed0b2458482607f36e3483e5d
Source dataset
uspto-grants-1995_08
Patent number
US05446040

Reaction notes

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