Hydrochloric Acid → HCID 13457909, compound

HRID 462731Notes

Reaction equation

HRID 462731 reaction equation
B.[C:2]([N:7]1[CH2:26][CH2:25][N:10]2[CH2:11][C@@H:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[C:18]([C@@H:9]2[CH2:8]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)(=O)[CH2:3][CH2:4][CH3:5].[ClH:27]>O1CCCC1>[ClH:27].[ClH:27].[CH2:2]([N:7]1[CH2:26][CH2:25][N:10]2[CH2:11][C@@H:12]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13]3[C:18]([C@@H:9]2[CH2:8]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 13457907HCID 13457907, compound

Product 1

HCID 13457909HCID 13457909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 M borane in tetrahydrofuran (100 ml) maintained under nitrogen at ambient temperature was added cis-1,3,4,6,7,11b-hexahydro-2-butyryl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline (8.6 g, 0.021 m) and and the mixtdre heated to reflux for 3 hours, then cooled in an ice bath and carefully treated with 20% 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 (3×50 ml). The extracts were dried over MgSO4 and evaporated to an oily residue. This was dissolved in methanol (50 ml) and isopropanol (50 ml) and acidified with HCl gas. The white solid, which precipitated immediately, was collected by filtration, recrystallized from methanol/ether, and vacuum dried at 90° for 24 hours to give 5.7 g of cis-1,3,4,6,7,11b-hexahydro- 2-butyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride, m.p. 261°-262°.

Workup

  1. temperaturethe mixtdre 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 (3×50 ml)
  9. dry with materialThe extracts were dried over MgSO4
  10. customevaporated to an oily residue
  11. dissolutionThis was dissolved in methanol (50 ml)
  12. customThe white solid, which precipitated immediately
  13. filtrationwas collected by filtration
  14. customrecrystallized from methanol/ether, and vacuum
  15. customdried at 90° for 24 hours

Sources & evidence

ORD record
ord-7a10c6404353440588b1d0c944d80da8
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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