Hydrochloric Acid → HCID 13457904, compound

HRID 462729Notes

Reaction equation

HRID 462729 reaction equation
B.[C:2]1([C@H:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@@H:11]3[CH2:18][N:19]([C:22](=O)[CH2:23][CH3:24])[CH2:20][CH2:21][N:10]3[CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>O1CCCC1>[ClH:26].[ClH:26].[C:2]1([C@H:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@@H:11]3[CH2:18][N:19]([CH2:22][CH2:23][CH3:24])[CH2:20][CH2:21][N:10]3[CH2:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 13457902HCID 13457902, compound

Product 1

HCID 13457904HCID 13457904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 M borane in tetrahydrofuran (55 ml) maintained under nitrogen at 0° C. was added cis-1,3,4,6,7,11b-hexahydro-7-phenyl-2-propionyl-2H-pyrazino[ 2,1-a]isoquinoline (5.3 g, 0.016 m) and the mixture heated to reflux for 3 hours, then cooled in an ice bath and carefully treated with 10% HCl (100 ml). This mixture was heated to reflux for 1 hour, then cooled, and the tetrahydrofuran removed on an aspirator. The remaining aqueous solution was basified to pH 11 with 50% NaOH and extracted with chloroform. The extracts were dried over MgSO4 and evaporated to a solid residue (6.0 g). This was dissolved in methanol (50 ml) and isopropanol (50 ml) and acidified with HCl gas. Upon cooling and standing, a white solid crystallized, which was collected by filtration and vacuum dried at 80° for 24 hours to give 4.6 g cis-1,3,4,6,7,11b-hexahydro-7-phenyl-2-propyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride, m.p. 273°-274°.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled in an ice bath
  4. temperatureThis mixture was heated
  5. temperatureto reflux for 1 hour
  6. temperaturecooled
  7. customthe tetrahydrofuran removed on an aspirator
  8. extractionextracted with chloroform
  9. dry with materialThe extracts were dried over MgSO4
  10. customevaporated to a solid residue (6.0 g)
  11. dissolutionThis was dissolved in methanol (50 ml)
  12. temperatureUpon cooling
  13. customa white solid crystallized
  14. filtrationwhich was collected by filtration and vacuum
  15. customdried at 80° for 24 hours

Sources & evidence

ORD record
ord-9d955e9419e54847b6cac89728216d9b
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

Loading…