Hydrochloric Acid → HCID 13457933, compound

HRID 462736Notes

Reaction equation

HRID 462736 reaction equation
[CH3:1][N:2]1[CH2:24][CH2:23][N:5]2[CH2:6][C@@H:7]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[C:8]3[C:13]([C@@H:4]2[CH2:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[ClH:25]>CO.O.[Pd]>[ClH:25].[ClH:25].[CH3:1][N:2]1[CH2:24][CH2:23][N:5]2[CH2:6][C@@H:7]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[C:8]3[C:13]([C@@H:4]2[CH2:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 13457931HCID 13457931, compound

Product 1

HCID 13457933HCID 13457933, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of cis-1,3,4,6,7,11b-hexahydro-2-methyl-7-(4-nitrophenyl)-2H-pyrazino[2,1-a)isoquinoline (5.2 g, 0.014 m) in methanol (500 ml), water (100 ml) and conc HCl (5 ml) was hydrogenated on a Parr apparatus over 2.0 g of palladium on carbon catalyst of 40 psi for 1 hour. The catalyst was removed by filtration and the solvents evaporated to a solid residue. This was dissolved in water (500 ml), basified to pH 11 with 50% NaOH, and extracted with ether (3×200 ml). The extracts were dried over MgSO4 and evaporated to an oil, 4.04 g. This crude product was purified by chromatography on silica gel with a Prep 500 HPLC, eluting with 2% ammoniated methanol/chloroform. Pure fractions were combined and evaporated to give an oil, 1.12 g. This was dissolved in methanol (30 ml) and acidified with HCl gas. Upon standing, a white solid crystallized, which was collected by filtration and vacuum dried at 95% for 24 hours to give 1.08 g of cis-1,3,4,6,7,11b-hexahydro-2-methyl-7-(4-aminophenyl)-2H-pyrazino[2,1-a]isoquinoline dihydrochloride, m.p. 274°-276°.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents evaporated to a solid residue
  3. dissolutionThis was dissolved in water (500 ml)
  4. extractionextracted with ether (3×200 ml)
  5. dry with materialThe extracts were dried over MgSO4
  6. customevaporated to an oil, 4.04 g
  7. customThis crude product was purified by chromatography on silica gel with a Prep 500 HPLC
  8. washeluting with 2% ammoniated methanol/chloroform
  9. customevaporated
  10. customto give an oil, 1.12 g
  11. customa white solid crystallized
  12. filtrationwhich was collected by filtration and vacuum
  13. customdried at 95% for 24 hours

Sources & evidence

ORD record
ord-56fba91f605447699a4d833befacec45
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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