1,3-Propanediamine → 1-(3-Aminopropylamino)-4-methoxyanthracene-9,10-dione

HRID 330059

반응식

HRID 330059 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[CH3:6][O:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:23])[C:12]=2[C:11](OC)=[CH:10][CH:9]=1>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:11]1[C:12]2[C:13](=[O:23])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:22])[C:21]=2[C:8]([O:7][CH3:6])=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 4281,3-PropanediamineHCID 2660541,4-Dimethoxyanthraquinone

생성물 1

HCID 133805771-(3-Aminopropylamino)-4-methoxyanthracene-9,10-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1,3-diaminopropane (2.07 g, 28 mmol) and 1,4 dimethoxyanthraquinone (1.50 g, 5.6 mmol) in freshly distilled CH2Cl2 (1.5 l) was fitted with a reflux condenser, and irradiated with a sunlamp for 6 h. The solvent was distilled and the crude mixture was dried in vacuo overnight. The crude product was triturated with warm petroleum ether to remove excess amine. Chromatography (silica gel CCl4 and CH2Cl2, 1:1) was performed by slowly increasing the polarity of the solvent to CH2Cl2 to remove the unreacted 1,4-dimethoxyanthraquinone. Upon elution with methanol, a purple band slowly developed. A purple oil remained upon removal of the solvent. The oil was extracted with warm CCl4, and crystallized by adding petroleum ether to the combined CCl4 extracts. Crystallization afforded a purple solid, 0.48 g (28%) in three crops. Recrystallization from a mixture of CCl4 and petroleum ether afforded an analytical sample: mp 108°-110° C.; 1H NMR (CDCl3)δ9.95 (broad t, 1H), 8.21-8.25 (m, 2 H), 7.68-7.73 (m, 2 H), 7.37 (d, 1 H), 7.17 (d, 1H), 4.00(s, 3 H), 3.39-3.48 (m, 2 H), 2.94 (t,2 H), 1.86-1.98 (m, 2 H), 1.36 (broad s, 2H). Anal. Calcd. for C18H18N2O3 : C, 69.66; H, 5.85, N, 9.03. Found: C, 69.75; H 5.95; N, 8.95.

후처리

  1. customirradiated with a sunlamp for 6 h
  2. distillationThe solvent was distilled
  3. dry with materialthe crude mixture was dried in vacuo overnight
  4. customThe crude product was triturated with warm petroleum ether
  5. customto remove excess amine
  6. temperatureby slowly increasing the polarity of the solvent to CH2Cl2
  7. customto remove the unreacted 1,4-dimethoxyanthraquinone
  8. washUpon elution with methanol
  9. customA purple oil remained upon removal of the solvent
  10. extractionThe oil was extracted with warm CCl4
  11. customcrystallized
  12. additionby adding petroleum ether to the combined CCl4
  13. customCrystallization
  14. customafforded a purple solid, 0.48 g (28%) in three crops
  15. customRecrystallization
  16. additionfrom a mixture of CCl4 and petroleum ether
  17. customafforded an analytical sample

출처 및 근거

ORD 기록
ord-53d5eeeede6f49438551dc0d9f136c20
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894451

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