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 1105553Notes

Reaction equation

HRID 1105553 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12219N-MethylethylamineHCID 5003444Sodium cyanoborohydride2×HCID 128324091-(2-oxo-propyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Product 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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

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 additional 1.7 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°.

Workup

  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

Sources & evidence

ORD record
ord-bfca4bfc085c42f78eda71ab13a9ed26
Source dataset
uspto-grants-1982_01
Patent number
US04309345

Reaction notes

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