Methane → HCID 68577138, compound

HRID 2390922Notes

Reaction equation

HRID 2390922 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][N:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][CH2:12][N:11]2CC=C)=[CH:6][CH:5]=1.Cl.C.[OH-].[Na+]>[Ru](Cl)(Cl)Cl.C1(C)C=CC=CC=1.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[NH:11][CH2:12][CH2:13][N:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:15]2)=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68576882HCID 68576882, compound

Product 1

HCID 68577138HCID 68577138, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To (R)-2-(4-chlorophenyl)-4-phenyl-1-(2-propenyl)hexahydropyrazine dihydrochloride (285 mg, 0.87 mmol) produced in Example 21, distilled water (2 mL), conc. hydrochloric acid (181 mg, 2.0 equivalents), ruthenium chloride (9 mg, 0.04 equivalent) and activated charcoal (9 mg) were added. The mixture was stirred at 100° C. for 18 hours. Toluene (4 mL) and 30 wt % aqueous solution of sodium hydroxide (258 mg, 2.2 equivalents) were added thereto. The formed insolubles were removed by filtration, and washed with toluene (2 mL). After the organic layer and aqueous layer of the filtrate were separated, the organic layer was washed twice with distilled water (6 mL). The organic layer was concentrated and dried under vacuum, to obtain 89 mg of the title compound as brown oil (yield: 29%, chemical purity: 83.8 area %). The retention time in the chemical purity analysis method was 3.7 min.

Workup

  1. additionwere added
  2. customThe formed insolubles were removed by filtration
  3. washwashed with toluene (2 mL)
  4. customAfter the organic layer and aqueous layer of the filtrate were separated
  5. washthe organic layer was washed twice with distilled water (6 mL)
  6. concentrationThe organic layer was concentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8d241b3e39544b0e91dd1ac2f230a379
Source dataset
uspto-grants-2012_09
Patent number
US08273883B2

Reaction notes

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