Hydrochloric Acid → HCID 13457907, compound

HRID 462730Notes

Reaction equation

HRID 462730 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:34])[CH2:31][CH2:32][CH3:33].Cl>C(Cl)(Cl)Cl.O1CCCC1>[C:30]([N:20]1[CH2:21][CH2:22][N:11]2[CH2:10][C@@H:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:18]3[C:13]([C@@H:12]2[CH2:19]1)=[CH:14][CH:15]=[CH:16][CH:17]=3)(=[O:34])[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 13457899HCID 13457899, compound

Product 1

HCID 13457907HCID 13457907, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of cis-1,3,4,6,7,11b-hexahydro-7-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride (7.8 g, 0.023 m) and triethylamine (9.4 g, 0.93 m) in chloroform (100 ml) maintained at 0° under nitrogen was added dropwise butyryl chloride (3.8 g, 0.0356 m). The mixture was allowed to warm to ambient temperature and stirred for 3 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 an oily residue which was dissolved in tetrahydrofuran (100 ml) and a white solid crystallized which was collected by filtration to give 5.1 g of cis-1,3,4,6,7,11b-hexahydro-2-butyryl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline, m.p. 212°-213°. An additional 3.5 of good purity product was recovered from the tetrahydrofuran to give a total of 8.6 g (93%).

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with 10% HCl (2×50 ml), water (50 ml)
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent
  5. customgave an oily residue which
  6. customa white solid crystallized which
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-fe85a9acf2e648689745bd92d62a0752
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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