Ethyl Bromide → 3-(Naphthalen-2-yloxy)propan-1-amine

HRID 1793494Notes

Reaction equation

HRID 1793494 reaction equation
COC1C=CC([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)=CC=1.C(Br)C>CC(C)=O>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[O:13][CH2:12][CH2:11][CH2:10][NH2:9]

Participants

4

Reactant 2

HCID 6332Ethyl BromideHCID 9839556(4-Methoxyphenyl)-(3-(naphthalen-2-yloxy)propyl)amine

Product 1

HCID 167907513-(Naphthalen-2-yloxy)propan-1-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(4-methoxyphenyl)-[3-(naphthalen-2-yloxy)propyl]amine (0.5 gm, 0.002 mole) and ethyl bromide(0.52 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-ethyl [3-(naphthalen-2-yloxy)propylamine, crystallized as yellow oil, (yield 0.64 gm, 94.6%).

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-c7a8b54195494acfa10a4169a5ff2089
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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