Morpholine → HCID 15053198, compound

HRID 1088825Notes

Reaction equation

HRID 1088825 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][CH3:23])[CH2:19][CH:18]([C:24](O)=[O:25])[CH2:17]2.C(N(CC)CC)C.ClC(OCC)=O.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>O1CCCC1>[N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:1][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][CH3:23])[CH2:19][CH:18]([C:24]([N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[O:25])[CH2:17]2

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15053197HCID 15053197, compound

Product 1

HCID 15053198HCID 15053198, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(2-benzimidazolyl)thiomethyl-1-ethyl-1,2,3,4-tetrahydroquinoline-3-carboxylic acid (1.3 g) in tetrahydrofuran (50 ml) were added dropwise triethylamine (0.4 g) and ethyl chloroformate (0.4 g) with stirring under ice-cooling and the mixture was stirred for 30 minutes. Moreover morpholine (0.4 g) was added dropwise thereto and the mixture was stirred for 3 hours at room temperature. The solvent was distilled off and the resulting residue was dissolved in chloroform. The solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:dichloromethane-methanol (200:1)], and recrystallized from ethyl acetate-ethanol to give 8-(2-benzimidazolyl)thiomethyl-3-morpholinocarbonyl-1-ethyl-1,2,3,4-tetrahydroquinoline (0.7 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringthe mixture was stirred for 3 hours at room temperature
  4. distillationThe solvent was distilled off
  5. dissolutionthe resulting residue was dissolved in chloroform
  6. washThe solution was washed with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe resulting residue was purified by silica gel column chromatography [eluent:dichloromethane-methanol (200:1)]
  10. customrecrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-43ff4375dbb9418e822371af7cb6a3a4
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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