HCID 86755695, compound → HCID 86755694, compound

HRID 1872767Notes

Reaction equation

HRID 1872767 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15]3[N:19]([CH3:20])[C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[N:16]=3)[CH2:10][C@@H:9]2[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)C=CC=CC=1>CO.[Pd]>[CH3:20][N:19]1[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]=[C:15]1[NH:14][C@H:11]1[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:10]1

Participants

4

Reactant 1

HCID 86755695HCID 86755695, compound

Product 1

HCID 86755694HCID 86755694, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-cis-N-[1,2-bis(phenylmethyl)-4-piperidinyl]-1-methyl-1H-benzimidazol-2-amine (4.7 g) in methanol (200 ml) was hydrogenated with palladium on activated carbon (10%; 2 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent evaporated. The residue was suspended in DIPE, filtered and dried, yielding 0.6 g (17%) of (±)-cis-1-methyl-N-[2-(phenylmethyl)-4-piperidinyl]-1H-benzimidazol-2-amine (interm. 31; mp. 86.3° C.).

Workup

  1. filtrationAfter uptake of hydrogen, the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  4. customThe pure fractions were collected
  5. customthe solvent evaporated
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-935a4a95077e41dfbcb63ae39a697b6f
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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