Chloroform → Nicardipine Hydrochloride

HRID 622175

反応式

HRID 622175 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([OH:22])=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4].O[CH2:26][CH2:27][N:28]([CH3:36])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)(Cl)[Cl:53]>>[ClH:53].[CH3:23][C:8]1[NH:7][C:6]([CH3:24])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]=1[C:20]([O:22][CH2:26][CH2:27][N:28]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:36])=[O:21]

参加物

5

反応物 4

HCID 6212ChloroformHCID 10868DicyclohexylcarbodiimideHCID 66876N-Benzyl-N-methylethanolamineHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

生成物 1

HCID 41114Nicardipine Hydrochloride収率 85.4%

実験手順

A mixture of 3-methoxycarbonyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid (3.32 g, 0.01 mole), N-(2-hydroxyethyl)-N-benzyl-methylamine (4.98 g) and N,N'-dicyclohexylcarbodiimide (DCC) (2.05 g) is stirred at 60°-80° C. for 1 hour. To the reaction mixture chloroform (16 ml) is added and the mixture is washed with water (3×50 ml). Then the organic layer is washed with a 10% aqueous solution of HCl (16 ml) and water (3×10 ml). The organic layer is dried with anhydrous Na2SO4 and the solvent is evaporated in vacuo. The oily residue is dissolved in ethyl acetate (18 ml) and stirred at 0° C. for 2 hours. The precipitate, which separates, is filtered off, dried in vacuo and recrystallized from acetone. Thus, there is obtained the title compound nicardipine hydrochloride (4.4 g, 85.4%).

後処理

  1. washthe mixture is washed with water (3×50 ml)
  2. washThen the organic layer is washed with a 10% aqueous solution of HCl (16 ml) and water (3×10 ml)
  3. dry with materialThe organic layer is dried with anhydrous Na2SO4
  4. customthe solvent is evaporated in vacuo
  5. dissolutionThe oily residue is dissolved in ethyl acetate (18 ml)
  6. stirringstirred at 0° C. for 2 hours
  7. filtrationis filtered off
  8. customdried in vacuo
  9. customrecrystallized from acetone

出典と根拠

ORDレコード
ord-7b6da278485948ff8040dbb04421b14c
出典データセット
uspto-grants-1988_09
特許番号
US04769465

関連ノート

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