trans-4-[(Phenylmethyl)amino]-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinol → trans-4-Amino-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinol

HRID 1165042Notes

Reaction equation

HRID 1165042 reaction equation
C1(C[NH:8][C@@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:11][C@H:10]2[OH:24])C=CC=CC=1.[H][H]>[Pd].CO>[NH2:8][C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18]2[N:19]=[CH:20][CH:21]=[CH:22][N:23]=2)[CH2:11][C@H:10]1[OH:24]

Participants

5

Reactant 2

HCID 14854947trans-4-[(Phenylmethyl)amino]-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinolHCID 178418361HCID 178418361, compound

Product 1

HCID 67833360trans-4-Amino-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinolYield 86.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10.6 parts of trans-4-[(phenylmethyl)amino]-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinol and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 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, saturated with ammonia, (90:10 by volume) as eluent. The second fraction was collected and the eluent was evaporated, yielding 6.6 parts (86.9%) of trans-4-amino-1-[2-(2-pyrimidinylamino)ethyl]-3-piperidinol as a residue (interm. 19).

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
  5. customThe second fraction was collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-498642c8a8d24257981e0363e5479c02
Source dataset
uspto-grants-1990_03
Patent number
US04906643

Reaction notes

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