HCID 21421186, compound → HCID 21421185, compound

HRID 1579114Notes

Reaction equation

HRID 1579114 reaction equation
Cl.[C:2]([C:4]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:5]=1[O:6][CH2:7][CH:8]([OH:15])[CH2:9][NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:3]>CO.N.[Ni]>[NH2:3][CH2:2][C:4]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:5]=1[O:6][CH2:7][CH:8]([OH:15])[CH2:9][NH:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 1

HCID 21421186HCID 21421186, compound

Product 1

HCID 21421185HCID 21421185, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

6.3 gm (0.02 mol) of 1-(2-cyano-4-chlorophenoxy)-2-hydroxy-3-tert.-butylamino propane hydrochloride were dissolved in 100 ml of methanol containing 10 ml of NH3 and the mixture was hydrogenated under normal pressure at 20°C over Raney-nickel. After separation of the catalyst, the solvent was distilled off in vacuo, and the residue was admixed with ether and water. After an addition of a small amount of NaOH, the aqueous phase was separated and the organic phase was washed with water and dried over MgSO4. After distilling off the ether, a solid residue remained which was recrystallized from ethyl acetate with an addition of petroleum ether to obtain 1-(2-aminomethyl-4-chlorphenoxy)-2-hydroxy-3-tert.-butylamino propane. The base was dissolved in ethanol and ethereal HCl was added thereto. The precipitated crystals of the hydrochloride of the base were isolated to obtain 3.1 gm of the hydrochloride having a melting point of 118° - 120°C.

Workup

  1. customAfter separation of the catalyst
  2. distillationthe solvent was distilled off in vacuo
  3. additionAfter an addition of a small amount of NaOH
  4. customthe aqueous phase was separated
  5. washthe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. distillationAfter distilling off the ether
  8. customwas recrystallized from ethyl acetate with an addition of petroleum ether

Sources & evidence

ORD record
ord-7f05a6381b904031b0d2ed7964a949fb
Source dataset
uspto-grants-1976_02
Patent number
US03940489

Reaction notes

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