Hydrochloric Acid → HCID 13457912, compound

HRID 462732Notes

Reaction equation

HRID 462732 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:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].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:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 13457899HCID 13457899, compound

Product 1

HCID 13457912HCID 13457912, compoundYield 76.3%

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, 0.093 m) in chloroform (100 ml) maintained at 0° under nitrogen was added dropwise hexanoyl chloride (4.79 g, 0.0356 m). The mixture was allowed to warm to ambient temperature and stirred for 3 hours, then treated with 10% HCl (25 ml). The layers were separated and the organic phase washed with 10% HCl (2×25 ml), water and dried over MgSO4. Evaporation of the solvent gave an oily residue which was dissolved in tetrahydrofuran and a white solid crystallized which was collected by filtration to give 6.4 g of cis-1,3,4,6,7,11b-hexahydro-2-hexanoyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline, m.p. 163°-164.5°. An additional 3.1 g of good purity product was recovered from the tetrahydrofuran to give a total of 9.5 g.

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with 10% HCl (2×25 ml), water
  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-285b1b4fe6624469a4104af79c936daa
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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