6-(4-{3-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexanenitrile → Ammonia

HRID 1433261Notes

Reaction equation

HRID 1433261 reaction equation
[CH:1]([N:4]([CH:33]([CH3:35])[CH3:34])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32])[CH:17]=[CH:18][C:19]=1[OH:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2]>C(O)C.[Ni]>[NH3:4].[NH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][CH2:22][CH2:21][C:16]1[CH:17]=[CH:18][C:19]([OH:20])=[C:14]([C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([CH:33]([CH3:34])[CH3:35])[CH:1]([CH3:3])[CH3:2])[CH:15]=1

Participants

5

Reactant 1

HCID 579332016-(4-{3-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexanenitrile

Product 2

HCID 222AmmoniaHCID 579332174-{4-[(6-Aminohexyl)oxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

6-(4-{3-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexanenitrile (Preparation 25, 783 mg, 1.64 mmol) was dissolved in ethanol (20 ml) and Raney nickel (100 mg) added. The reaction was hydrogenated under 60 psi at 40° C. for 18 hours, cooled to room temperature and the reaction filtered through Arbocel™ and the filtrate solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (90/10/1.0 by volume) to furnish the title compound, 506 mg.

Workup

  1. filtrationthe reaction filtered through Arbocel™
  2. customthe filtrate solvent removed in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-0f57a7953fa44e5bbfbab4523e8b71d3
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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