Phenethylamine → N-(2-Phenylethyl)naphthalen-1-amine

HRID 1833971Notes

Reaction equation

HRID 1833971 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[C:34]1([CH2:40][CH2:41][NH2:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O>[C:34]1([CH2:40][CH2:41][NH:42][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 7540Triphenyl phosphiteHCID 86632-Naphthol

Product 1

HCID 15775221N-(2-Phenylethyl)naphthalen-1-amineYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

288 parts of β-naphthol, 9 parts of triphenyl phosphite and 270 parts of 2-phenylethylamine are heated to 180° C whilst stirring. The elimination of water commences at this temperature and has ended after 5 hours at an internal temperature of 240° C. 36 parts of water are collected in the water separator. After distilling off excess β-naphthol and amine under reduced pressure, 2-phenylethyl-naphthylamine distils, at a boiling point of 230° - 231° C/5 mm Hg. 479 parts of 2-phenylethyl-naphthylamine are obtained, corresponding to a yield of 97% of theory.

Workup

  1. custom36 parts of water are collected in the water separator
  2. distillationAfter distilling off excess β-naphthol and amine under reduced pressure, 2-phenylethyl-naphthylamine
  3. customdistils, at a boiling point of 230° - 231° C/5 mm Hg

Sources & evidence

ORD record
ord-f3056816a92649b295b9c3b50568f49c
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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