1,2-Ethanediamine, N1-phenyl- → 1-[2-Hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-(2-anilino-ethylamino)-piperidine

HRID 614363Notes

Reaction equation

HRID 614363 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][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[H][H]>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][CH:28]=[CH:27][CH:26]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 742701,2-Ethanediamine, N1-phenyl-HCID 233473441-[2-Hydroxy-(2-methoxyphenyloxy)-propyl]-piperidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 233473391-[2-Hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-(2-anilino-ethylamino)-piperidine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 16.7 g of 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-piperidine-4-one and 10.5 g of N-(2-aminoethyl)-aniline in 250 ml of methanol, with the addition of 1 g of a 5% platinum on charcoal catalyst is hydrogenated at room temperature and under normal pressure until 1 molar equivalent of hydrogen has been taken up. The catalyst is thereafter removed by filtration and the filtrate is concentrated under reduced pressure. The residue is freed from excess starting material in a bulb tube at 0.3 mm Hg and 120° C oven temperature to yield as distillation residue 1-[2-hydroxy-3-(2-methoxyphenyloxy)-propyl]-4-(2-anilino-ethylamino)-piperidine, which can be used without further purification.

Workup

  1. customThe catalyst is thereafter removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is freed from excess starting material in a bulb tube at 0.3 mm Hg and 120° C oven temperature

Sources & evidence

ORD record
ord-19ba23c697d24fa38c5f7227883ba5e1
Source dataset
uspto-grants-1979_03
Patent number
US04144344

Reaction notes

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