HCID 70416117, compound → HCID 70416551, compound

HRID 2231208Notes

Reaction equation

HRID 2231208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]1[CH2:13][N:14]([CH3:19])[C:15](=O)[C:16](=O)[N:8]1[C@@H:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:6]2.[ClH:26].Cl.COC1C=C2C(=CC=1)[C@H]1CN(C)CCN1[C@@H](C1C=CC=CC=1)C2>>[ClH:26].[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]1[CH2:13][N:14]([CH3:19])[CH2:15][CH2:16][N:8]1[C@@H:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:6]2

Participants

3

Reactant 2

HCID 70416117HCID 70416117, compoundHCID 70416556HCID 70416556, compound

Product 1

HCID 70416551HCID 70416551, compound

Procedure

Cis-1,3,4,6,7,11b-hexahydro-9-methoxy-2-methyl-6-methyl-2H-pyrazino[2,1-a]isoquinoline-3,4-dione (16.0 g, 0.04 mol) was added with stirring to a solution of 1M borane in tetrahydrofuran (350 ml) under nitrogen and the resulting mixture was refluxed for 4 hrs, then cooled to 0° C., and then treated with 10% HCl (150 ml). The mixture was refluxed for 1 hr and cooled, and then the solvent was evaporated. The aqueous residue was basified to pH 11 with 50% NaOH and extracted with chloroform (3×250 ml). The combined chloroform extracts were dried over MgSO4 and evaporated to an oily residue. The residue was dissolved in methanol/isopropanol (150 ml) and acidified with HCl gas. A solid salt crystallized (10.3 g) which was recrystallized from methanol (300 ml) and water (10 ml) to give 9.8 g of cis-1,3,4,6,7,11b-hexahydro-9-methoxy-2-methyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride as an off-white solid. An analytical sample had mp. 274°-275° C. Following the same procedure and substituting trans-1,3,4,6,7,11b-hexahydro-9-methoxy-2-methyl-6-phenyl-2H-pyrazino[2,1-a]isoquinoline-3,4-dione for cis-1,3,4,6,7,11b-hexahydro-9-methoxy-2-methyl-6-phenyl-2H-pyrazino[2,1-a]isoquinoline-3,4-dione, trans-1,3,4,6,7,11b-hexahydro-9-methoxy-2-methyl-6-phenyl-2H-pyrazino[2,1-a]isoquinoline dihydrochloride may be obtained.

Workup

  1. custommay be obtained

Sources & evidence

ORD record
ord-a074c60b738443a38a809b4d17929d20
Source dataset
uspto-grants-1988_11
Patent number
US04782058

Reaction notes

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