Hydrochloric Acid → Dimethyl-[2-(4-pyridin-4-yl-phenoxy)-ethyl]-amine

HRID 271581Notes

Reaction equation

HRID 271581 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Cl[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18].Cl>C(Cl)(Cl)Cl>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79012-Chloro-N,N-dimethylethylamineHCID 1354101774-(Pyridin-4-yl)phenol

Product 1

HCID 17968254Dimethyl-[2-(4-pyridin-4-yl-phenoxy)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1 g of 4-pyridin-4-yl-phenol, 1.3 g of (2-chloro-ethyl)-dimethyl-amine.HCl and 2.42 g of K2CO2 were heated for 48 h under reflux. The mixture was diluted with chloroform, washed with brine and dried over MgSO4. After evaporation to dryness the residue was chromatographed on silicagel with CH2Cl2/MeOH/NH3conc=90:10:1 to give dimethyl-[2-(4-pyridin-4-yl-phenoxy)-ethyl]-amine as brown powder.

Workup

  1. temperatureunder reflux
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customAfter evaporation to dryness the residue
  5. customwas chromatographed on silicagel with CH2Cl2/MeOH/NH3conc=90:10:1

Sources & evidence

ORD record
ord-703704d54f9647a6aaaf8fef7329dd72
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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