Water → 2-Phenyl-1-(pyridin-4-yl)ethan-1-amine dihydrochloride

HRID 464321Notes

Reaction equation

HRID 464321 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:3][CH:2]=1.Cl.[NH2:17]O.O>N1C=CC=CC=1>[C:10]1([CH2:9][CH:7]([NH2:17])[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 110417042-Phenyl-1-(pyridin-4-yl)ethan-1-one

Product 1

HCID 99903262-Phenyl-1-(pyridin-4-yl)ethan-1-amine dihydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.34 g of benzyl 4-pyridyl ketone and 3.75 g of hydroxylamine hydrochloride in 50 ml of pyridine are heated to boiling for 4 hours. After cooling, the mixture is stirred into 600 ml of water, and the oxime (5.6 g) of melting point 194°-196° C. is filtered off. The oxime is hydrogenated with hydrogen in isopropanol with Raney nickel at 50° C. and under normal pressure. After the customary working up, the amine is obtained as a pale yellow oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe oxime (5.6 g) of melting point 194°-196° C. is filtered off
  3. customis hydrogenated with hydrogen in isopropanol with Raney nickel at 50° C. and under normal pressure

Sources & evidence

ORD record
ord-a35641b4173d4471ae1f172793f25ca3
Source dataset
uspto-grants-1985_10
Patent number
US04547508

Reaction notes

Loading…