Triethylamine → HCID 19030728, compound

HRID 483543Notes

Reaction equation

HRID 483543 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:24]3[CH2:23][CH2:22][CH2:21][C:20](=[O:25])[C:19]=3[CH2:18][CH2:17][C:15]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:24]3[C:19](=[C:20]([OH:25])[CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][C:15]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimide2×HCID 19030764HCID 19030764, compound

Product 1

HCID 19030728HCID 19030728, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(1-Benzyl-4-piperidinyl)-5-oxo-3,4,5,6,7,8-hexahydrocarbostyril (10.0 g) is dissolved in chloroform (500 ml) and thereto is added N-bromosuccinimide (5.78 g). The mixture is refluxed with stirring for 2 hours. Thereto are added N-bromosuccinimide (5.00 g) and triethylamine (50 ml) and the mixture is refluxed with stirring for 3 hours. After cooling, the reaction mixture is washed twice with 30% aqueous sodium thiosulfate solution (200 ml) and once with saline solution (500 ml) and then dried with magnesium sulfate. The solvent is evaporated off and the resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=40:1) and recrystallized from ethanol/water to give 1-(1-benzyl-4-piperidinyl)-5-hydroxy-3,4-dihydrocarbostyril (2.13 g) as colorless needles, m.p.: 183°-184° C.

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturethe mixture is refluxed
  3. stirringwith stirring for 3 hours
  4. temperatureAfter cooling
  5. washthe reaction mixture is washed twice with 30% aqueous sodium thiosulfate solution (200 ml) and once with saline solution (500 ml)
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent is evaporated off
  8. customthe resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=40:1)
  9. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-142dd7e9dd544bf3abef2a4d53404c74
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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