1-[2-Hydroxy-(2-methoxyphenyloxy)-propyl]-piperidin-4-one → 1-[2-Hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-[2-(4-pyridyl-amino)-ethylamino]-piperidine

HRID 614366Notes

Reaction equation

HRID 614366 reaction equation
[OH:1][CH:2]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1.[NH2:21][CH2:22][CH2:23][NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CO.[Pt]>[OH:1][CH:2]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:21][CH2:22][CH2:23][NH:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 233473441-[2-Hydroxy-(2-methoxyphenyloxy)-propyl]-piperidin-4-oneHCID 233473554-(2-Aminoethylamino)-piperidine

Product 1

HCID 233473521-[2-Hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-[2-(4-pyridyl-amino)-ethylamino]-piperidine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 27.9 g of 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-piperidin-4-one and 22.8 g of 4-(2-aminoethylamino)-piperidine in 250 ml of methanol, with the addition of 2 g of a platinum on charcoal catalyst, is hydrogenated at room temperature and under normal pressure until 1 molar equivalent has been taken up. The catalyst is thereafter removed by filtration and the filtrate is concentrated under reduced pressure. The residue is dissolved in 500 ml of methylene chloride and the solution is washed with three 150 ml portions of water, dried over sodium sulphate and concentrated under reduced pressure to yield 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-[2-(4-pyridyl-amino)-ethylamino]-piperidine, which can be processed without further purification.

Workup

  1. customis hydrogenated at room temperature and under normal pressure until 1 molar equivalent
  2. customThe catalyst is thereafter removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in 500 ml of methylene chloride
  5. washthe solution is washed with three 150 ml portions of water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5adf209b5b9244a290577080b993ccbb
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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