2-(3-Cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran → 2-(3-(3,4-Dichlorophenyl)-4-aminobutyl)oxytetrahydropyran

HRID 1611663Notes

Reaction equation

HRID 1611663 reaction equation
[C:1]([CH:3]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)[CH2:4][CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)#[N:2]>[Ni].CCO.[OH-].[NH4+]>[Cl:20][C:15]1[CH:14]=[C:13]([CH:3]([CH2:1][NH2:2])[CH2:4][CH2:5][O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

5

Reactant 1

HCID 156708072-(3-Cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran

Product 1

HCID 156708082-(3-(3,4-Dichlorophenyl)-4-aminobutyl)oxytetrahydropyranYield 54.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

Raney nickel (38 g) was placed in a stainless steel bottle and EtOH (100 ml) was added followed by a solution of 2-(3-cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran (138 g, 0.44 mol) in EtOH (1100 ml) and concentrated ammonium hydroxide (600 ml). The bottle was then shaken under an atmosphere of hydrogen gas (53 psi) and when the pressure fell below 35 psi the flask was repressurised. After 24 h the pressure remained constant so the reaction mixture was filtered through Celite™ and concentrated. Water was added, the mixture was extracted with DCM and then dried (Na2SO4) and concentrated to give 2-(3-(3,4-dichlorophenyl)-4-aminobutyl)oxytetrahydropyran as an oil (75 g, 0.24 mol).

Workup

  1. additionwas added
  2. filtrationwas filtered through Celite™
  3. concentrationconcentrated
  4. additionWater was added
  5. extractionthe mixture was extracted with DCM
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9b156c49bd694ef7b70894df0cd31c73
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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