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Nifedipine → N-Methylnifedipine

HRID 399373
노트
인쇄 미리보기

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HRID 399373 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 4485NifedipineHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2회

생성물 1

HCID 14817573N-Methylnifedipine

시약·촉매·용매 3

HCID 7909Methyl Isobutyl Ketone용매
HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매

반응 조건

온도
38 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-df6e601094554948acb93bc45d40cf8c
출처 데이터셋
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05820944

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