Ethanol → HCID 21223446, compound

HRID 1584108Notes

Reaction equation

HRID 1584108 reaction equation
C1([C:7]2[N:16]3[C:10]([C:11](=O)[C:12]4[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=4[CH2:14][CH2:15]3)=[N:9][N:8]=2)C=CC=CC=1.[H][H].[CH2:24](O)[CH3:25]>[Pd]>[CH3:10][N:16]1[CH2:25][CH2:24][CH:13]([CH:11]2[C:12]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[CH2:14][CH2:15][N:9]3[N:8]=[CH:7][N:16]=[C:10]23)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 702EthanolHCID 21223462HCID 21223462, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21223446HCID 21223446, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Compound (5) (0.00767 mol) in ethanol (200 ml) was hydrogenated with palladium on activated carbon (2.2 g) as a catalyst at 50° C. over a 5 hours period under a 3 bar pressure in a Parr apparatus. After uptake of hydrogen (1 eq.), the catalyst was filtered through celite and the filtrate was evaporated. The residue (2.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 94/6/0.5 to 90/10/0.5) (15-40 μm). The pure fractions were collected and evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 1.22 g (83%) of (±)-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-[1,2,4]triazolo[5,1-b][3]benzazepine; mp. 133.8° C. (comp. 44).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue (2.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 94/6/0.5 to 90/10/0.5) (15-40 μm)
  3. customThe pure fractions were collected
  4. customevaporated
  5. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-f25ae196d66e43ae99440f523306aff0
Source dataset
uspto-grants-1999_08
Patent number
US05932569

Reaction notes

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