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

HRID 1678858

反応式

HRID 1678858 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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 hydrochloride 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.).

後処理

  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

出典と根拠

ORDレコード
ord-c1c78d3f98f14d8dba0e59276f8fcc7c
出典データセット
uspto-grants-1978_03
特許番号
US04077959

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