HCID 15096760, compound → cis-1-(1H-benzimidazol-2-ylmethyl)-3-methoxy-4-piperidinamine dihydrate
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]([NH:17]CC2C=CC=CC=2)[C@H:13]([O:25][CH3:26])[CH2:12]1.[H][H]>[Pd].CO>[OH2:25].[OH2:25].[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:25][CH3:26])[CH2:12]1Participants
Procedure
A mixture of 18 parts of cis-1-(1H-benzimidazol-2-ylmethyl)-3-methoxy-N-(phenylmethyl)-4-piperidinamine and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10%. 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 (93:7 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue solidified slowly and the solid product was suspended in 2,2'-oxybispropane. The product was filtered off and dried at the air, yielding 6 parts of cis-1-(1H-benzimidazol-2-ylmethyl)-3-methoxy-4-piperidinamine dihydrate:mp. 92.0° C. (intermediate 122).
Workup
- filtrationthe catalyst was filtered off
- customthe filtrate was evaporated
- customThe residue was purified by column-chromatography over silica gel using
- additiona mixture of trichloromethane and methanol (93:7 by volume)
- customThe pure fractions were collected
- customthe eluent was evaporated
- filtrationThe product was filtered off
- customdried at the air
Sources & evidence
- ORD record
- ord-cbaa81cc7fd34804863aae716cdf7ba7
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137896
Reaction notes
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