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Diethyl Ether → methyl N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate

HRID 247096
ノート
印刷プレビュー

反応式

HRID 247096 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH2:24][CH2:25]Cl)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[C:28]1([CH:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:35][CH2:36][NH2:37])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OCC)C>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH2:24][CH2:25][NH:37][CH2:36][CH2:35][CH:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 796983,3-DiphenylpropylamineHCID 30168882-Chloroethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

生成物 1

HCID 10769981methyl N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate収率 40.5%

試薬・触媒・溶媒 1

HCID 7237
O-Xylene
溶媒

実験手順

A solution comprising 5.92 g of methyl 2-chloroethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)- pyridine-3,5-dicarboxylate and 9.50 g of 3,3-diphenylpropylamine in 20 ml of xylene was refluxed under stirring for 105 minutes. The mixture was then cooled. By dilution with diethyl ether a semisolid compound was obtained, and it was separated from the liquid by decantation. The residue was treated with diethyl ether at 0°-4° C. and the supernatant was decanted. This procedure was repeated until a solid was obtained, and this was collected by filtration. Mother liquors and washings from the decantation were collected and evaporated to dryness under vacuum. The residue was chromatographed on a silica gel column (270 g) using a mixture of chloroform and acetone as eluent. Pure fractions were combined and the solvent was evaporated off. The residue was dissolved in diethyl ether and hydrogen chloride in diethyl ether was added. The solid (3.92 g) was crystallized from ethyl acetate or isopropyl acetate and recrystallized from ethyl acetate to give 3.46 g of the title compound, m.p. 128°-32° C.

後処理

  1. temperaturewas refluxed
  2. temperatureThe mixture was then cooled
  3. customit was separated from the liquid by decantation
  4. additionThe residue was treated with diethyl ether at 0°-4° C.
  5. customthe supernatant was decanted
  6. customwas obtained
  7. filtrationthis was collected by filtration
  8. customMother liquors and washings from the decantation were collected
  9. customevaporated to dryness under vacuum
  10. customThe residue was chromatographed on a silica gel column (270 g)
  11. additiona mixture of chloroform and acetone as eluent
  12. customthe solvent was evaporated off
  13. dissolutionThe residue was dissolved in diethyl ether
  14. additionhydrogen chloride in diethyl ether was added
  15. customThe solid (3.92 g) was crystallized from ethyl acetate or isopropyl acetate
  16. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-de4c5d2b509d4b938261320decae8deb
出典データセット
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04705797

反応ノート

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