Potassium Hydroxide → 9,9-Dimethyl-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-YL)-2-pyrrolin-2-YL]acridan

HRID 1764221

반응식

HRID 1764221 반응식
CC1NC(=O)CC1.P(Cl)(Cl)(Cl)=O.CC1(C)C2C=CC=CC=2NC2C1=CC=CC=2.[OH-].[K+].Cl.[CH3:32][C:33]1([CH3:59])[C:46]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[N:40]([C:47]2[N:48]([C:53]3[CH2:57][CH2:56][CH:55]([CH3:58])[N:54]=3)[CH:49]([CH3:52])[CH2:50][CH:51]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2>ClCCCl>[CH3:59][C:33]1([CH3:32])[C:46]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[N:40]([C:47]2[N:48]([C:53]3[CH2:57][CH2:56][CH:55]([CH3:58])[N:54]=3)[CH:49]([CH3:52])[CH2:50][CH:51]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2

참가 물질

7

반응물 5

HCID 14797Potassium HydroxideHCID 226479,9-Dimethyl-9,10-dihydroacridineHCID 24813Phosphorus oxychlorideHCID 660555-Methyl-2-pyrrolidoneHCID 203071649,9-Dimethyl-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-YL)-2-pyrrolin-2-YL]acridan hydrochloride

생성물 1

HCID 127994009,9-Dimethyl-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-YL)-2-pyrrolin-2-YL]acridan수율 35%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of 5-methyl-2-pyrrolidinone (2.0 g., 0.02 mole) and phosphorus oxychloride (3.0 g., 0.02 mole) in 15 ml. of 1,2-dichloroethane after standing 15 hr. at room temperature is combined with 9,9-dimethylacridan (2.1 g., 0.01 mole) after a 48 hr. period is added to 30 ml. of 5N potassium hydroxide and 30 g. of crushed ice. The 1,2-dichloroethane fraction is separated, extracted with 50 ml. of 1.5N hydrochloric acid and 50 ml. of water and dried over magnesium sulfate. Concentration of the 1,2-dichloroethane solution provides a residue which is stirred with 100 ml. of ether and filtered. The filter cake containing crude hydrochloride salt of the product is stirred with sodium hydroxide solution affording the free base. Crystallization from n-heptane provides 1.3 g. (35% yield) of 9,9-DIMETHYL-10-[5-METHYL-1-(5-METHYL-1-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]ACRIDAN, m.p. 135°-139° C. from which the hydrochloride salt is prepared according to the procedure of Example 1. Analytically pure 9,9-DIMETHYL-10-[5-METHYL-1-(5-METHYL-1-PYRROLIN-2-YL)-2-PYRROLIN-2-YL]ACRIDAN HYDROCHLORIDE, from acetone-ether, has a melting point of 247.5°-248.0° C. (corr.).

후처리

  1. additionperiod is added to 30 ml
  2. customThe 1,2-dichloroethane fraction is separated
  3. extractionextracted with 50 ml
  4. dry with materialof water and dried over magnesium sulfate
  5. customConcentration of the 1,2-dichloroethane solution provides a residue which
  6. filtrationof ether and filtered
  7. additionThe filter cake containing crude hydrochloride salt of the product
  8. stirringis stirred with sodium hydroxide solution
  9. customaffording the free base
  10. customCrystallization from n-heptane
  11. customprovides 1.3 g

출처 및 근거

ORD 기록
ord-2387daadb0714cfba31a867a29854118
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04115571

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