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

HRID 46529

Reaktionsgleichung

Reaktionsgleichung von HRID 46529
Cl.[CH:2]([NH:5][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)([CH3:4])[CH3:3].[CH:27](=O)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C([BH3-])#N.[Na+].Cl>C(#N)C.C(O)(=O)C>[CH:2]([N:5]([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)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8130HeptanalHCID 5003444Sodium cyanoborohydrideHCID 205555941-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride

Produkt 1

HCID 128324391-[2-(N-isopropyl-N-heptylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2.66 ml of glacial acetic acid are added dropwise to the ice-cooled mixture of 5.0 g of slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride, 15.2 g of heptaldehyde, 2.52 g of sodium cyanoborohydride and 53 ml of acetonitrile. The mixture is stirred at room temperature for 2 hours, cooled, acidified to pH=1 with concentrated hydrochloric acid and evaporated to remove the acetonitrile. The residue is diluted with water, the solution washed with diethyl ether, basified to pH=10-11 with 3 N aqueous sodium hydroxide and extracted with chloroform. The extract is dried, evaporated and the residue crystallized from ethanol-water (5:2) to give the 1-[2-(N-isopropyl-N-heptylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, RR racemate melting at 102°-104°.

Aufarbeitung

  1. temperaturecooled
  2. additionmixture of 5.0 g
  3. temperaturecooled
  4. customevaporated
  5. customto remove the acetonitrile
  6. additionThe residue is diluted with water
  7. washthe solution washed with diethyl ether
  8. extractionextracted with chloroform
  9. customThe extract is dried
  10. customevaporated
  11. customthe residue crystallized from ethanol-water (5:2)

Quellen und Nachweise

ORD-Eintrag
ord-ef102dcd7a7e4fc9ad48367195f4048e
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173633

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