P-Anisidine → HCID 9994541, compound

HRID 1793465Notes

Reaction equation

HRID 1793465 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[O:26][CH2:27][CH2:28]Cl>CS(C)=O.O>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:28][CH2:27][O:26][C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 3498772-(2-Naphthyloxy)-1-chloroethane

Product 1

HCID 9994541HCID 9994541, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.45 gm, 0.003 mole) was taken in dry dimethylsulphoxide (DMSO, 40 ml). Now 2-(2-naphthyloxy)-1-chloroethane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 145° C. for 7 hrs. The reaction was completed as checked by TLC. Reaction mixture was poured in distilled water (60 ml) and extracted with ethyl acetate thrice. The organic layer was separated and concentrated to get oily compound which was later crystallized by benzene hexane to get N-(4-methoxyphenyl)-[2-(naphthalen-2-yloxy) ethyl] amine yellow solid, m.p. 92° C., (yield 0.67 gm, 94%).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted with ethyl acetate thrice
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customto get oily compound which
  7. customwas later crystallized by benzene hexane

Sources & evidence

ORD record
ord-fc70e18baee047c6b3a9f591ed865c1a
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

Loading…