Hydrochloric Acid → HCID 13457914, compound

HRID 462733Notes

Reaction equation

HRID 462733 reaction equation
B.[C:2]([N:9]1[CH2:28][CH2:27][N:12]2[CH2:13][C@@H:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[C:20]([C@@H:11]2[CH2:10]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)(=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[ClH:29]>O1CCCC1>[ClH:29].[ClH:29].[CH2:2]([N:9]1[CH2:28][CH2:27][N:12]2[CH2:13][C@@H:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15]3[C:20]([C@@H:11]2[CH2:10]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 13457912HCID 13457912, compound

Product 1

HCID 13457914HCID 13457914, 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-hexanoyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline (8.3 g, 0.019 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 residue was treated with 20% NaOH (300 ml) and extracted with chloroform (3×75 ml). The extracts were dried over MgSO4 and evaporated to an oily residue, 12.3 g. This was dissolved in methanol (100 ml) and isopropanol (50 ml) and acidified with HCl gas. A white solid crystallized which was collected by filtration, recrystallized from methanol/water, and vacuum dried at 110° for 24 hours to give 7.1 g cis-1,3,4,6,7,11b-hexahydro-2-hexyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride, m.p. 221°-222°.

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. additionThe residue was treated with 20% NaOH (300 ml)
  9. extractionextracted with chloroform (3×75 ml)
  10. dry with materialThe extracts were dried over MgSO4
  11. customevaporated to an oily residue, 12.3 g
  12. dissolutionThis was dissolved in methanol (100 ml)
  13. customA white solid crystallized which
  14. filtrationwas collected by filtration
  15. customrecrystallized from methanol/water, and vacuum
  16. customdried at 110° for 24 hours

Sources & evidence

ORD record
ord-00800a8ca8b149d8b3e984c85d21008c
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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