Isopropylamine → 9-Carbamoyl-9-(3-isopropylaminopentyl)fluorene

HRID 542643

反応式

HRID 542643 の反応式
[C:1]([C:4]1([CH2:17][CH2:18][C:19](=O)[CH2:20][CH3:21])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].[CH:23]([NH2:26])([CH3:25])[CH3:24].[H][H]>[Pd].CO>[C:1]([C:4]1([CH2:17][CH2:18][CH:19]([NH:26][CH:23]([CH3:25])[CH3:24])[CH2:20][CH3:21])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2]

参加物

6

反応物 3

HCID 6363IsopropylamineHCID 138534899-Carbamoyl-9-(3-oxopentyl)fluoreneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 138534939-Carbamoyl-9-(3-isopropylaminopentyl)fluorene

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A mixture of 14.6 g. of 9-carbamoyl-9-(3-oxopentyl)fluorene from Example 7 and 14.8 g. of isopropylamine in 100 ml. of methanol containing 3.7 g. of 5% palladium on charcoal was heated at 80° C. for eight hours at 750 psi hydrogen. The reaction mixture was cooled, filtered and concentrated to a volume of about 25 ml. The product was added to ethyl acetate and diethyl ether. The organic solution was extracted with 6N hydrochloric acid. The acidic extracts were combined, cooled in ice and made alkaline by addition of 10% sodium hydroxide. The alkaline solution was extracted several times with 50% ethyl acetate in diethyl ether. The extracts were combined, washed with water, dried and concentrated to dryness to provide 4.0 g. of the title compound. The product was dissolved in 50 ml. of ethyl acetate and stirred while 1.38 g. of maleic acid were added. The precipitated solid was collected by filtration and dried to afford 4.0 g. of 9-carbamoyl-9-(3-isopropylaminopentyl)fluorene maleate. m.p. 161°-163° C.

後処理

  1. additionA mixture of 14.6 g
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated to a volume of about 25 ml
  5. additionThe product was added to ethyl acetate and diethyl ether
  6. extractionThe organic solution was extracted with 6N hydrochloric acid
  7. temperaturecooled in ice
  8. additionby addition of 10% sodium hydroxide
  9. extractionThe alkaline solution was extracted several times with 50% ethyl acetate in diethyl ether
  10. washwashed with water
  11. customdried
  12. concentrationconcentrated to dryness
  13. customto provide 4.0 g

出典と根拠

ORDレコード
ord-bd72797b1ef94e9a8ce95fdc38782af8
出典データセット
uspto-grants-1987_04
特許番号
US04658061

関連ノート

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