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

HRID 46527노트

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HRID 46527 반응식
[CH3:1][NH:2][CH2:3][CH3:4].O=[C:6]([CH3:26])[CH2:7][C:8]1[C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[C:14]=12.C([BH3-])#N.[Na+].[ClH:31]>C(#N)C.C(O)(=O)C>[ClH:31].[CH2:3]([N:2]([CH:6]([CH3:26])[CH2:7][C:8]1[C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[C:14]=12)[CH3:1])[CH3:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 12219N-MethylethylamineHCID 5003444Sodium cyanoborohydride2회HCID 128324091-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

생성물 1

HCID 205555921-[2-(N-ethyl-N-methylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

Compound No. 26 may also be prepared as follows: 8.5 ml of glacial acetic acid are added to the solution of 8.9 g of N-methyl-ethylamine in 100 ml of acetonitrile, followed by 7.5 g of 1-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one and 1.7 g of sodium cyanoborohydride. The mixture is refluxed overnight, an additional1.7 g of sodium cyanoborohydride is added and refluxing is continued for an additional day. The mixture is cooled, acidified to pH=1 with hydrochloric acid and evaporated. Water is added to the residue, the mixture is washed with diethyl ether, filtered and the aqueous filtrate basified to pH=10-11 with 3 N aqueous sodium hydroxide. It is extracted with chloroform, the extract dried, evaporated and the residue is dissolved in the minimum amount of ethanol. The solution is combined with 2.15 ml of 8 N ethanolic hydrochloric acid, the precipitate collected and recrystallized from ethanol, to yield the 1-[2-(N-ethyl-N-methylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride, melting at 256°-257°.

후처리

  1. custom26 may also be prepared
  2. temperatureThe mixture is refluxed overnight
  3. temperaturerefluxing
  4. waitis continued for an additional day
  5. temperatureThe mixture is cooled
  6. customevaporated
  7. additionWater is added to the residue
  8. washthe mixture is washed with diethyl ether
  9. filtrationfiltered
  10. extractionIt is extracted with chloroform
  11. customthe extract dried
  12. customevaporated
  13. dissolutionthe residue is dissolved in the minimum amount of ethanol
  14. customthe precipitate collected
  15. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-94ff7732a18d4dc79a33bc748a0dbf40
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04173633

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