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Nifedipine → N-Methylnifedipine

HRID 399373
ノート
印刷プレビュー

反応式

HRID 399373 の反応式
[CH3:1][C:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[N+:19]([O-:21])=[O:20])[C:3]=1[C:22]([O:24][CH3:25])=[O:23].[H-].[Na+].CI.[C:30](OCC)(=O)C>O1CCCC1.CC(CC(C)=O)C.CCCCCC>[CH3:1][C:2]1[N:7]([CH3:30])[C:6]([CH3:8])=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[C:22]([O:24][CH3:25])=[O:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 4485NifedipineHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2 回

生成物 1

HCID 14817573N-Methylnifedipine

試薬・触媒・溶媒 3

HCID 7909Methyl Isobutyl Ketone溶媒
HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

反応条件

温度
38 °C

実験手順

12 g of nifedipine was disclosed in 50 ml of tetrahydrofuran in a nitrogen atmosphere. 1.66 g of a sodium hydride/oil dispersion (60% NaH) was added under agitation. Following agitation for some time, 10 ml of methyl iodide was added, and the resulting mixture was agitated for 1 hour at 38° C. 200 ml of ethyl acetate was then added. The resulting organic layer was washed several times with water, and was then dehydrated with sodium sulfate. The sodium sulfate was filtered out, and the solvent was removed. The solid obtained was dissolved in 200 ml of MIBK, and hexane was added producing 8.9 g of N-methylnifedipine in the form of yellow crystals. This compound had a melting point of 184° to 187° C.; an infrared absorption spectrum of 1690 cm-1 ; C=O, 1524 cm-1 ; N--O), and a proton-NMR spectrum (solvent: CDCl3) of 2.5 (6 H, methyl), 3.3 (3H, N-methyl), 3.6 (6H, O-methyl), 5.7 (1H, C--H, 7.2-7.6 (4H, C--H in aromatic nucleus).

後処理

  1. additionwas added
  2. washThe resulting organic layer was washed several times with water
  3. filtrationThe sodium sulfate was filtered out
  4. customthe solvent was removed
  5. customThe solid obtained

出典と根拠

ORDレコード
ord-df6e601094554948acb93bc45d40cf8c
出典データセット
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05820944

反応ノート

読み込み中…

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