Benzylamine → HCID 69316771, compound

HRID 2217306Notes

Reaction equation

HRID 2217306 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18](=O)[CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]1.C1(C[NH2:30])C=CC=CC=1>CO.[Pd]>[NH2:30][CH:18]([CH:19]([CH3:21])[CH3:20])[CH2:17][N:14]1[CH2:15][CH2:16][CH:11]([NH:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 22036939HCID 22036939, compound

Product 1

HCID 69316771HCID 69316771, compoundYield 4.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[4-(1H-benzimidazol-2-ylamino)-1-piperidinyl]-3-methyl-2-butanone (0.03 mol) and benzenemethanamine (0.09 mol) in methanol (200 ml) was hydrogenated at 40° C. under a 3 bar pressure for 48 hours with palladium on activated carbon (1.3 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered through celite, washed with CH3OH and the filtrate was evaporated. Hydrogenation was continued for 24 hours. After uptake of hydrogen, the catalyst was filtered through celite, washed with CH3OH and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/14/1; 20-45 μm). The desired fractions were collected and the solvent was evaporated. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 0.4 g of (±)-N-[1-(2-amino-3-methylbutyl)4-piperidinyl]-1H-benzimidazol-2-amine; mp. 138° C. (interm. 37).

Workup

  1. filtrationAfter uptake of hydrogen, the catalyst was filtered through celite
  2. washwashed with CH3OH
  3. customthe filtrate was evaporated
  4. filtrationAfter uptake of hydrogen, the catalyst was filtered through celite
  5. washwashed with CH3OH
  6. customthe filtrate was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/14/1; 20-45 μm)
  8. customThe desired fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from diethyl ether
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-92e9ef95bc2c4c279df45e7974e782c3
Source dataset
uspto-grants-2008_08
Patent number
US07407969B2

Reaction notes

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