Hydrochloric Acid → HCID 13457919, compound

HRID 462734Notes

Reaction equation

HRID 462734 reaction equation
B.[C:2]([N:10]1[CH2:29][CH2:28][N:13]2[CH2:14][C@@H:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[C:21]([C@@H:12]2[CH2:11]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)(=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[ClH:30]>O1CCCC1>[ClH:30].[ClH:30].[CH2:2]([N:10]1[CH2:29][CH2:28][N:13]2[CH2:14][C@@H:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[C:21]([C@@H:12]2[CH2:11]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 13457917HCID 13457917, compound

Product 1

HCID 13457919HCID 13457919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 M borane in tetrahydrofuran (70 ml) maintained under nitrogen at 0° was added cis-1,3,4,6,7,11b-hexahydro-2-benzoyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline (6.8 g, 0.0184 m) and the mixture heated to reflux for 3 hours, then cooled in an ice bath and carefully treated with 10% HCl (50 ml). This mixture was heated to reflux for 1 hour, then cooled, and tetrahydrofuran removed on an aspirator. The residue was basified to pH 11 with 10% NaOH and extracted with chloroform (3×100 ml). The extracts were dried over MgSO4 and evaporated to a yellow oil, 7.8 g. This crude product was purified by chromatography on a Prep 500 HPLC on silica gel eluting with 1:1 ether:cyclohexane (1% diethylamine). The pure fractions were combined and evaporated to an oil which was dissolved in methanol (50 ml) and isopropanol (25 ml) and acidified with HCl gas. The white solid which crystallized was collected by filtration and vacuum dried at 80° for 24 hours to give 3.9 g of cis-1,3,4,6,7,11b-hexahydro-2-benzyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride, m.p. 203°-204°.

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. customtetrahydrofuran removed on an aspirator
  8. extractionextracted with chloroform (3×100 ml)
  9. dry with materialThe extracts were dried over MgSO4
  10. customevaporated to a yellow oil, 7.8 g
  11. customThis crude product was purified by chromatography on a Prep 500 HPLC on silica gel eluting with 1:1 ether
  12. customevaporated to an oil which
  13. dissolutionwas dissolved in methanol (50 ml)
  14. customThe white solid which crystallized
  15. filtrationwas collected by filtration and vacuum
  16. customdried at 80° for 24 hours

Sources & evidence

ORD record
ord-174e1a27f5b8459ebd488c591ed9654a
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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