Methylamine → HCID 14685792, compound

HRID 1088823Notes

Reaction equation

HRID 1088823 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][CH2:18][C:17]2=O.[CH3:25][NH2:26].[BH4-].[Na+]>CO>[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][CH2:18][CH:17]2[NH:26][CH3:25]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 14685766HCID 14685766, compound

Product 1

HCID 14685792HCID 14685792, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-(2-Benzimidazolyl)thiomethyl-1-ethyl-4-oxo-1,2,3,4-tetrahydroquinoline (1 g) and methylamine (40% methanol solution, 7.4 ml) were dissolved in methanol (15 ml) and the solution was refluxed for 14 hours. After allowing to cool, sodium borohydride (630 mg) was added by portions with stirring at room temperature, and the mixture was stirred for 1 hour at the same temperature. The solvent was distilled off and the resulting residue was extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was recrystallized from ethyl acetate to give 8-(2-benzimidazolyl)thiomethyl-1-ethyl-4-methylamino-1,2,3,4-tetrahydroquinoline (970 mg).

Workup

  1. temperaturethe solution was refluxed for 14 hours
  2. temperatureto cool
  3. stirringthe mixture was stirred for 1 hour at the same temperature
  4. distillationThe solvent was distilled off
  5. extractionthe resulting residue was extracted with dichloromethane
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6ecbfdb22f1243b5be1fcd3315b2a31b
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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