Sodium Hydroxide → HCID 14747672, compound

HRID 1609502Notes

Reaction equation

HRID 1609502 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH:13]=[CH:12]2)([OH:3])=O.ClC(OCC(C)C)=O.[CH:28]1([CH2:34][NH:35][CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH:28]1([CH2:34][N:35]([CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[CH:12]3)=[O:3])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 131126105-[(2-Oxo-1,2-dihydroquinolin-6-yl)oxy]pentanoic acidHCID 20081645HCID 20081645, compound

Product 1

HCID 14747672HCID 14747672, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.00 Grams of 6-(4-carboxybutoxy)carbostyril is suspended in 60 ml of chloroform. Thereto is added 1.40 g of DBu. The mixture is stirred for 30 minutes at room temperature. 1.05 g of isobutyl chloroformate is added with ice cooling. Then, there is dropwise added at room temperature 1.61 g of N-(cyclohexylmethyl)-N-[2-(1-pyrrolidinyl)ethyl]amine. The mixture is stirred for 3 hours at room temperature. Then, a 0.5N aqueous sodium hydroxide solution is added, and the mixture is stirred for 10 minutes. Extraction with chloroform is effected. The extract is washed with water and dried with anhydrous magnesium sulfate. The solvent is removed by evaporation. The resulting residue is purified by a silica gel column chromatography (chloroform:methanol=20:1) and recrystallized from diethyl ether to obtain 1.00 g of 6-[4-{N-cyclohexylmethyl-N-[2-(1-pyrrolidinyl)ethyl]aminocarbonyl}butoxy]carbostyril.

Workup

  1. additionThereto is added 1.40 g of DBu
  2. stirringThe mixture is stirred for 3 hours at room temperature
  3. stirringthe mixture is stirred for 10 minutes
  4. extractionExtraction with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent is removed by evaporation
  8. customThe resulting residue is purified by a silica gel column chromatography (chloroform:methanol=20:1)
  9. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-37e800b34ed741a0a18b41f5bf34802d
Source dataset
uspto-grants-1995_03
Patent number
US05401740

Reaction notes

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