Sodium Hydroxide → N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(pyridin-3-yl)-ethylamine

HRID 861440Notes

Reaction equation

HRID 861440 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:20][CH:21]([OH:29])[C:22]2[CH:23]=[CH:24][C:25](Cl)=[N:26][CH:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:20][CH:21]([OH:29])[C:22]2[CH:27]=[N:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 441036D-PsicoseHCID 19704231N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

Product 1

HCID 9907789N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(pyridin-3-yl)-ethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine (100 mg, 0.26 mmol) in ethanol (7 mL) with 5N sodium hydroxide (0.1 mL, 0.5 mmol) is degassed with argon prior to addition of Ni(R) (100 mg). The mixture is hydrogenated at 40 Psi for overnight and then the catalyst is filtered through Celite and washed with a small amount of ethanol. Evaporation of the filtrate gives the title compound.

Workup

  1. filtrationthe catalyst is filtered through Celite
  2. washwashed with a small amount of ethanol
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-f98495ded2be449cafd01dfcae651d3b
Source dataset
uspto-grants-1998_02
Patent number
US05714506

Reaction notes

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