Hydrochloric Acid → 1-(2-isopropylaminoethyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

HRID 46513ノート

反応式

HRID 46513 の反応式
B#B.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:25](=[CH:26][CH:27]=1)[C:11]1=[C:12]([CH2:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=O)[C:13](=[O:17])[NH:14][CH2:15][CH2:16][CH:10]1[CH2:9][CH2:8]2.Cl>O1CCCC1>[CH:22]([NH:21][CH2:19][CH2:18][C:12]1[C:13](=[O:17])[NH:14][CH2:15][CH2:16][CH:10]2[CH2:9][CH2:8][C:7]3[C:25](=[CH:26][CH:27]=[C:5]([O:4][CH3:3])[CH:6]=3)[C:11]=12)([CH3:23])[CH3:24]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 20555608[9-methoxy-2-oxo-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-1-yl]-N-isopropyl-acetamide

生成物 1

HCID 128324141-(2-isopropylaminoethyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

80 ml of 1 M diborane in tetrahydrofuran are added to the suspension of 6.8 g of [9-methoxy-2-oxo-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-1-yl]-N-isopropyl-acetamide in 100 ml of tetrahydrofuran while stirring under nitrogen at 0°. After 20 hours 60 ml of 3 N hydrochloric acid are added dropwise and the mixture is refluxed for one hour. The tetrahydrofuran is distilled off under reduced pressure and the remainder is diluted with water. The resulting precipitate is filtered off and re-extracted with hot water. The aqueous filtrate is washed with diethyl ether and basified with 3 N aqueous sodium hydroxide. The suspension is extracted with methylene chloride, the extract dried, evaporated and the residue recrystallized from acetone, to yield the 1-(2-isopropylaminoethyl)-3,4,5,5a,6,7-hexahydro-9-methoxy-2H-naphth[1,2-d]azepin-2-one melting at 147°-149°.

後処理

  1. temperaturethe mixture is refluxed for one hour
  2. distillationThe tetrahydrofuran is distilled off under reduced pressure
  3. additionthe remainder is diluted with water
  4. filtrationThe resulting precipitate is filtered off
  5. extractionre-extracted with hot water
  6. washThe aqueous filtrate is washed with diethyl ether
  7. extractionThe suspension is extracted with methylene chloride
  8. customthe extract dried
  9. customevaporated
  10. customthe residue recrystallized from acetone

出典と根拠

ORDレコード
ord-f120366d7e0f4236b19e9cdc21386e2d
出典データセット
uspto-grants-1979_11
特許番号
US04173633

反応ノート

読み込み中…