Hydrochloric Acid → HCID 13457902, compound

HRID 462728Notes

Reaction equation

HRID 462728 reaction equation
Cl.Cl.[C:3]1([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@@H:12]3[CH2:19][NH:20][CH2:21][CH2:22][N:11]3[CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH2:31][CH3:32].Cl>C(Cl)(Cl)Cl.CCOCC>[C:3]1([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@@H:12]3[CH2:19][N:20]([C:30](=[O:33])[CH2:31][CH3:32])[CH2:21][CH2:22][N:11]3[CH2:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 13457899HCID 13457899, compound

Product 1

HCID 13457902HCID 13457902, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution is cis-1,3,4,6,7,11b-hexahydro-7-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride (7.0 g, 0.20 m) and triethylamine (8.4 g, 0.08 m) in chloroform (100 ml) maintained at 0° under nitrogen was added dropwise propionyl chloride (2.9 g, 0.031 m). The mixture was allowed to warm to ambient temperature and stirred for 16 hours, then treated with 10% HCl (50 ml). The layers were separated and the organic phase washed with 10% HCl (2×50 ml), water (50 ml), and dried over MgSO4. Evaporation of the solvent gave a solid residue, which was slurred with ether and filtered to give 2.1 g cis-1,3,4,6,7,11b-hexahydro-7-phenyl-2-propionyl-2H-pyrazino[2,1-a]isoquinoline, m.p. 250°-251° . An additional 3.2 g of good purity product was recovered from the ether to give a total of 5.3 g (82%).

Workup

  1. temperaturemaintained at 0° under nitrogen
  2. customThe layers were separated
  3. washthe organic phase washed with 10% HCl (2×50 ml), water (50 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent
  6. customgave a solid residue, which
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7a75ac75ba6b4b7d8da0b6a64e2d228d
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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