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

HRID 1903194Notes

Reaction equation

HRID 1903194 reaction equation
[N+](C1C=CC(O[C:9]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20](=[O:25])[CH:19]=[CH:18]3)=[O:10])=CC=1)([O-])=O.[OH:28][CH2:29][CH2:30][NH:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C)C=O>[OH:28][CH2:29][CH2:30][N:31]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C:9]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH:19]=[CH:18]2)=[O:10]

Participants

4

Reactant 2

HCID 17827Ethanol, 2-(cyclohexylamino)-HCID 204681836-[3-(p-Nitrophenoxycarbonyl)propoxy]carbostyril

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.8 Grams of 6-[3-(p-nitrophenoxycarbonyl)propoxy]carbostyril was dissolved in 40 ml of dimethylformamide, then 1.6 ml of N-(2-hydroxyethyl)cyclohexylamine was added thereto and the reaction mixture was stirred at 60°-70° C. for 12 hours. After the reaction was completed, the solvent was removed by distillation and the residue thus obtained was purified by a silica-gel column chromatography [Silica-gel used was "Wako C-200" and the solvent used was a mixture of chloroform:methanol=20:1 (vol/vol)]. The crude crystals thus obtained was recrystallized from chloroform-petroleum ether to obtain 1.3 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril as in the form of colorless needle-like crystals. Melting point: 165°-166° C.

Workup

  1. customthe solvent was removed by distillation
  2. customthe residue thus obtained
  3. customwas purified by a silica-gel column chromatography [Silica-gel
  4. additiona mixture of chloroform
  5. customThe crude crystals thus obtained
  6. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-849c2eaf47ea4d51a24026d88b280d97
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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