HCID 15096761, compound → HCID 67914605, compound

HRID 846782Notes

Reaction equation

HRID 846782 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[CH2:16][CH2:15][C@H:14]([NH2:17])[C@H:13]([O:18][CH3:19])[CH2:12]1.[H][H]>C(O)(=O)C>[CH3:19][O:18][C@H:13]1[C@@H:14]([NH2:17])[CH2:15][CH2:16][N:11]([CH2:10][C:2]2[NH:1][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=3[N:3]=2)[CH2:12]1

Participants

4

Reactant 2

HCID 15096761HCID 15096761, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67914605HCID 67914605, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 9 parts of cis-1-(1H-benzimidazol-2-ylmethyl)-3-methoxy-4-piperidinamine and 150 parts of acetic acid was hydrogenated at normal pressure and at room temperature with 2 parts of rhodium-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) saturated with ammonia, as eluent. The second fraction was collected and the eluent was evaporated, yielding 5 parts of cis-3-methoxy-1-[(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-methyl]-4-piperidinamine as a residue (intermediate 113).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) saturated with ammonia
  5. customThe second fraction was collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0b94038323a24772a183710b6c3279aa
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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