Cyclopropylamine → 9-Carbamoyl-9-(3-cyclopropylaminopropyl)fluorene

HRID 542638

反応式

HRID 542638 の反応式
C(C1(CCC#N)C2C=CC=CC=2C2C1=CC=CC=2)(=O)N.C1(N)CC1.C(O)(=O)/C=C\C(O)=O.C(O)(=O)/C=C\C(O)=O.[C:41]([C:44]1([CH2:57][CH2:58][CH2:59][NH:60][CH:61]2[CH2:63][CH2:62]2)[C:56]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[C:50]2[C:45]1=[CH:46][CH:47]=[CH:48][CH:49]=2)(=[O:43])[NH2:42]>[Pd].C(OCC)(=O)C.C(O)C>[C:41]([C:44]1([CH2:57][CH2:58][CH2:59][NH:60][CH:61]2[CH2:63][CH2:62]2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:50]=2[C:51]2[C:56]1=[CH:55][CH:54]=[CH:53][CH:52]=2)(=[O:43])[NH2:42]

参加物

8

反応物 4

HCID 69828CyclopropylamineHCID 444266Maleic AcidHCID 30188199-(2-Cyanoethyl)-9H-fluorene-9-carboxamideHCID 704428029-Carbamoyl-9-(3-cyclopropylaminopropyl)fluorene maleate

生成物 1

HCID 138534919-Carbamoyl-9-(3-cyclopropylaminopropyl)fluorene

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of 4.6 g. of 9-carbamoyl-9-(2-cyanoethyl)fluorene in 200 ml. of ethanol containing 2.3 g. of 5% palladium on carbon and 10.0 g. of cyclopropylamine was stirred under hydrogen at 60 psi at 90° C. for sixteen hours. The reaction mixture was cooled to 25° C., filtered and concentrated to a volume of 20 ml. The oil was dissolved in 200 ml. of 50% ethyl acetate-diethyl ether and the solution was extracted with 6N hydrochloric acid. The acid layer was cooled and made alkaline by addition of 10% aqueous sodium hydroxide. The alkaline solution was extracted several times with fresh diethyl ether-ethyl acetate. The organic extracts were combined, washed with water, dried and the solvent was removed by evaporation to give 3.7 g. of the title comound as an oil. The oil was diluted by addition of 1.4 g. of maleic acid and the mixture was further diluted by addition of 50 ml. of ethyl acetate. The precipitated crystals were collected by filtration and dried to afford 1.5 g. of 9-carbamoyl-9-(3-cyclopropylaminopropyl)fluorene maleate. m.p. 163°-165° C.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated to a volume of 20 ml
  3. dissolutionThe oil was dissolved in 200 ml
  4. extractionof 50% ethyl acetate-diethyl ether and the solution was extracted with 6N hydrochloric acid
  5. temperatureThe acid layer was cooled
  6. additionby addition of 10% aqueous sodium hydroxide
  7. extractionThe alkaline solution was extracted several times with fresh diethyl ether-ethyl acetate
  8. washwashed with water
  9. customdried
  10. customthe solvent was removed by evaporation
  11. customto give 3.7 g
  12. additionThe oil was diluted by addition of 1.4 g
  13. filtrationThe precipitated crystals were collected by filtration
  14. customdried
  15. customto afford 1.5 g

出典と根拠

ORDレコード
ord-ec8246ab8aa8491694a98456405c4a39
出典データセット
uspto-grants-1987_04
特許番号
US04658061

関連ノート

読み込み中…