Dimethyl Sulfoxide → HCID 178511884, compound

HRID 369981Notes

Reaction equation

HRID 369981 reaction equation
Cl.Cl.Cl.[CH2:4]1[CH:17]2[N:8]([CH2:9][C:10]3[CH:11]=[C:12]([NH2:18])[CH:13]=[CH:14][C:15]=3[CH2:16]2)[CH2:7][CH2:6][NH:5]1.C[S:20](C)=O.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:4]1[CH:17]2[N:8]([CH2:9][C:10]3[CH:11]=[C:12]([NH:18][C:24]([C:25]4[S:20][CH:28]=[CH:27][CH:26]=4)=[NH:23])[CH:13]=[CH:14][C:15]=3[CH2:16]2)[CH2:7][CH2:6][NH:5]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 21584331HCID 21584331, compound

Product 1

HCID 178511884HCID 178511884, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 2,3,4,6,11,11a-hexahydro-1H-pyrazino[1,2-b]isoquinolin-8-amine trihydrochloride (1.8 g, 5.76 mmol) and methyl sulfoxide (20 ml) was added pyridine (0.94 ml) followed by S-methyl-2-thiophenethiocarboximide hydrochloride (2.13 g). The mixture was heated at 50° C., with stirring, for 7 h. The reaction mixture was then poured into water (150 ml) and, after stirring for 1 hour, the mixture was clarified by filtration. The filtrate was basified with 2.5N sodium hydroxide solution but no precipitate formed. An attempt to extract the product into dichloromethane caused the product to crystallize from the mixture. The product was isolated, washed with dichloromethane and dried; yield 1.28 g. This material was purified by chromatography using silica gel and 7% methanol saturated with ammonia in dichloromethane to yield N-(2,3,4,6,11,11a-hexahydro-1H-pyrazino[1,2-b]isoquinolin-8-yl)-2-thiophenecarboximidamide (0.83 g), m.p. 228° C. (dec.), MS 313 (M+H)+.

Workup

  1. stirringafter stirring for 1 hour
  2. filtrationthe mixture was clarified by filtration
  3. customno precipitate formed
  4. extractionAn attempt to extract the product into dichloromethane
  5. customto crystallize from the mixture
  6. customThe product was isolated
  7. washwashed with dichloromethane
  8. customdried
  9. customThis material was purified by chromatography

Sources & evidence

ORD record
ord-ab8d2f2827bc47c194dc89863f84e39c
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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