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Ethanol → N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

HRID 1903195
Notes
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Reaction equation

HRID 1903195 reaction equation
C(O)C.C(O[C:7]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH:17]=[CH:16]2)=[O:8])C.CC[O-].[Na+].[OH:28][CH2:29][CH2:30][NH:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)(Cl)Cl>[OH:28][CH2:29][CH2:30][N:31]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C:7]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH:17]=[CH:16]2)=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 17827Ethanol, 2-(cyclohexylamino)-HCID 2723922Sodium ethoxideHCID 128192626-(3-Ethoxycarbonylpropoxy)carbostyril

Product 1

HCID 12866343N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent

Procedure

Into 100 ml of ethanol were added 2.7 g of 6-(3-ethoxycarbonylpropoxy)carbostyril, 0.5 g of sodium ethylate and 5 ml of N-(2-hydroxyethyl)cyclohexylamine and reacted in an autoclave under a pressure of 110 atomospher at 140°-150° C. for 6 hours. After the reaction was completed, the reaction mixture was cooled and was concentrated under a reduced pressure. The residue thus obtained was dissolved in 200 ml of chloroform and washed with 1% K2CO3 aqueous solution, a diluted hydrochloric acid and water in this order, then dried with anhydrous sodium sulfate. Then the solvent was removed by distillation and the residue thus obtained was purified by a silica-gel column chromatography [the silica-gel used as Wako C-200, and the solvent used was a mixture of chloroform:methanol=20:1 (V/V)]. The crude crystals thus obtained was recrystallized from chloroform-petroleum ether to obtain 0.9 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril as in the form colorless needle-like crystals. Melting point: 165°-166° C.

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationwas concentrated under a reduced pressure
  3. customThe residue thus obtained
  4. washwashed with 1% K2CO3 aqueous solution
  5. dry with materiala diluted hydrochloric acid and water in this order, then dried with anhydrous sodium sulfate
  6. customThen the solvent was removed by distillation
  7. customthe residue thus obtained
  8. customwas purified by a silica-gel column chromatography [the silica-gel
  9. additiona mixture of chloroform
  10. customThe crude crystals thus obtained
  11. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-40d746cdf2ac40aea3c2d0d3ae691725
Source dataset
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04435404

Reaction notes

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