Methyl iodide → N-(4 methoxyphenyl)-N-methyl (3-(naphthalen-2-yloxy)propyl)amine

HRID 1793493Notes

Reaction equation

HRID 1793493 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[CH:5][CH:4]=1.[CH3:24]I>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH3:24])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 9839556(4-Methoxyphenyl)-(3-(naphthalen-2-yloxy)propyl)amine

Product 1

HCID 11723603N-(4 methoxyphenyl)-N-methyl (3-(naphthalen-2-yloxy)propyl)amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (4-methoxyphenyl)-[3-(naphthalen-2-yloxy)propyl]amine (0.5 gm, 0.002 mole) and methyl iodide (0.49 ml, 0.003 mole) was taken in dry acetone (40 ml). It was refluxed for 12 hrs and the progress of reaction checked by TLC. Reaction mixture was filtered and the filtrate was concentrated to get oily compound which was further crystallized by benzene hexane mixture to get N-(4 methoxyphenyl)-N-methyl (3-(naphthalen-2-yloxy)propyl) amine, crystallized as yellow solid, m.p. 112° C., (yield 0.69 gm, 94%)

Workup

  1. temperatureIt was refluxed for 12 hrs
  2. customthe progress of reaction
  3. customReaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customto get oily compound which
  7. customwas further crystallized by benzene hexane mixture

Sources & evidence

ORD record
ord-b5c41d7fab414a0c80ca766a87813d22
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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