P-Anisidine → (4-Methoxyphenyl)-(3-(naphthalen-2-yloxy)propyl)amine

HRID 1793462Notes

Reaction equation

HRID 1793462 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][CH2:29]Cl>CN(C=O)C.O>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:29][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 116872053-(2-Naphthyloxy)-1-chloropropane

Product 1

HCID 9839556(4-Methoxyphenyl)-(3-(naphthalen-2-yloxy)propyl)amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of anhydrous potassium carbonate (10 gm, in excess) and p-anisidine (0.42 gm, 0.003 mole) was taken in dry DMF (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and 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)-[3-(naphthalen-2-yloxy) propyl]amine as yellow solid, m.p. 110° C., (yield 0.64 gm, 92.5%).

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-0c6366e473ff4c269f7ad5920603d475
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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