Methanol → HCID 21421185, compound

HRID 259304Notes

Reaction equation

HRID 259304 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][CH2:8][CH:9](O)[NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:3].C[OH:22]>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:22])[CH2:9][NH:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 887MethanolHCID 21424196HCID 21424196, compound

Product 1

HCID 21421185HCID 21421185, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

6.3 gm (0.02 mol) of 1-(2-cyano-4-chlorophenoxy)-3-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-1ef62b739a884ce4aa226575735344c2
Source dataset
uspto-grants-1977_07
Patent number
US04036988

Reaction notes

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