Triethylamine → 1-(Quinoxalin-6-ylcarbonyl)-1,2,3,6-tetrahydropyridine

HRID 650543

Reaction equation

HRID 650543 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CC(C)(C)C(Cl)=O.[NH:28]1[CH2:33][CH:32]=[CH:31][CH2:30][CH2:29]1>C(Cl)Cl.C(OCC)C.CCCCCC>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([N:28]3[CH2:29][CH:30]=[CH:31][CH2:32][CH2:33]3)=[O:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 127501,2,3,6-TetrahydropyridineHCID 62493Pivaloyl chlorideHCID 674813Quinoxaline-6-carboxylic acid

Product 1

HCID 116300791-(Quinoxalin-6-ylcarbonyl)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

6-Quinoxalinecarboxylic acid (320 mg; 1.8 mmol) is suspended in 10 ml methylene chloride. As the suspension is stirred, 2 equivalents of triethylamine are added, followed by 0.22 ml (1.8 mmol) of trimethylacetyl chloride. After 15 min, 164 ul (1.8 mmol) of 1,2,3,6-tetrahydropyridine is added and the solution is stirred overnight. The solution is diluted with 20 ml of diethyl ether and washed with 10 ml water followed by 10 ml 10% NaCO3. The organic solution is dried over Na2SO4/K2CO3 and concentrated to a red-brown oil. Purification by chromatography on silica gel (eluted with CCl4/CHCl3 1:1) gives a pale yellow oil that eventually solidifies. The solid is layered with hexane and finely dispersed by mechanical crushing to yield pale yellow XIII. EMIS m/z=239 (parent), 157 (base), and 129. 1H NMR δ 2.22 and 2.34 (br, 2), 3.54, 3.94, 3.97, and 4.29 (br, 4), 5.5-6.0 (br, 2), 7.85 (dd, 1, J=8.7, 1.3 Hz), 8.15 (d, 1, J=1.6 Hz), 8.18 (br d, 1, J=8.5 Hz), and 8.90 ppm (s, 1).

Workup

  1. stirringthe solution is stirred overnight
  2. washwashed with 10 ml water
  3. dry with materialThe organic solution is dried over Na2SO4/K2CO3
  4. concentrationconcentrated to a red-brown oil
  5. customPurification by chromatography on silica gel (eluted with CCl4/CHCl3 1:1)
  6. customgives a pale yellow oil that
  7. additionfinely dispersed
  8. customby mechanical crushing

Sources & evidence

ORD record
ord-2f4d6131594340e4be215b218846e8ce
Source dataset
uspto-grants-2001_08
Patent number
US06274600B1

Linked notes

Loading…