Hydrochloric Acid → HCID 13457896, compound

HRID 462726Notes

Reaction equation

HRID 462726 reaction equation
B.[CH2:2]([N:4]1[C:23](=O)[C:22](=O)[N:7]2[CH2:8][C@@H:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[C:15]([C@@H:6]2[CH2:5]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:3].[ClH:26]>O1CCCC1>[ClH:26].[ClH:26].[CH2:2]([N:4]1[CH2:23][CH2:22][N:7]2[CH2:8][C@@H:9]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:10]3[C:15]([C@@H:6]2[CH2:5]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 70423865HCID 70423865, compound

Product 1

HCID 13457896HCID 13457896, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 M borane in tetrahydrofuran (200 ml) maintained under nitrogen at ambient temperature was added cis-1,3,4,6,7,11b-hexahydro-2-ethyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline-3,4-dione (9.9 g, 0.03 m) and the mixture heated to reflux for 2 hours. The mixture was cooled in an ice bath and carefully treated with 10% HCl (125 ml), refluxed for 1 hour, and the solvent removed on an aspirator. The residue was treated with water (300 ml), basified to pH 11 with 50% NaOH, and extracted with chloroform. The extracts were dried over MgSO4 and evaporated to a pale yellow oil. This oil was dissolved in methanol (100 ml) and isopropanol (100 ml) and acidified with HCl gas. Upon cooling and standing, a white solid crystallized which was collected by filtration. Recrystallization and vacuum drying gave 4.0 g of cis-1,3,4,6,7,11b-hexahydro-2-ethyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride, m.p. 276°-277° C. The product has an ad cyc H rating greater than 1×10-5M, a (3H)mepyramine rating of 3.4×10-7 and a (3H)QNB rating of 1.1×10-6M.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled in an ice bath
  4. temperaturerefluxed for 1 hour
  5. customthe solvent removed on an aspirator
  6. additionThe residue was treated with water (300 ml)
  7. extractionextracted with chloroform
  8. dry with materialThe extracts were dried over MgSO4
  9. customevaporated to a pale yellow oil
  10. dissolutionThis oil was dissolved in methanol (100 ml)
  11. temperatureUpon cooling
  12. customa white solid crystallized which
  13. filtrationwas collected by filtration
  14. customRecrystallization and vacuum
  15. customdrying

Sources & evidence

ORD record
ord-17383ab3edc3446f890d3c10013466d5
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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