Ethanol → HCID 23355056, compound

HRID 234616Notes

Reaction equation

HRID 234616 reaction equation
[N:1]1[N:2]=[CH:3][N:4]2[CH:10]=[CH:9][C:8]3[CH:11]=[CH:12][S:13][C:7]=3[CH2:6][C:5]=12.[CH2:14](O)[CH3:15]>C(O)(=O)C.[Pd]>[CH3:3][N:4]1[CH2:15][CH2:14][CH:7]([CH:6]2[C:7]3[S:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][N:1]3[N:2]=[CH:3][N:4]=[C:5]23)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 702EthanolHCID 23355043HCID 23355043, compound

Product 1

HCID 23355056HCID 23355056, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of compound (10) (0.00342 mol) and compound (9) (0.00342 mol) was hydrogenated in acetic acid (1.65 ml) and ethanol (150 ml) with palladium on activated carbon (2 g) as a catalyst at 50° C. overnight under a 3 bar pressure in a Parr apparatus. The catalyst was filtered through celite and the filtrate was evaporated till dryness. The residue was taken up in dichloromethane and washed with potassium carbonate 10%. The organic layer was dried (MgSO4), filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 90/10/1) (15-40 μm). The pure fractions were collected and evaporated. The residue (1.5 g) was crystallized from 2,2'-oxybispropane, yielding 0.92 g (76%) of (±)-6,10-dihydro-10-(1-methyl-4-piperidinyl)-5H-thieno[2,3-d][1,2,4]triazolo[1,5-a]azepine; mp. 123.4° C. (comp. 11).

Workup

  1. customat 50° C.
  2. customovernight
  3. filtrationThe catalyst was filtered through celite
  4. customthe filtrate was evaporated till dryness
  5. washwashed with potassium carbonate 10%
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered off
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 90/10/1) (15-40 μm)
  10. customThe pure fractions were collected
  11. customevaporated
  12. customThe residue (1.5 g) was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-f06c9d9b645048b1babf3dce36e679fa
Source dataset
uspto-grants-1997_01
Patent number
US05595988

Reaction notes

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