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

HRID 1833978Notes

Reaction equation

[C:1]1([CH2:7][CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([NH2:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[C:1]1([CH2:7][CH2:8][NH:20][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 210 °C

Procedure

122 parts of phenylethyl alcohol, 250 parts of α-naphthylamine and 10 parts of triphenyl phosphite are mixed and heated to 210° C. The elimination of water commences at this temperature. The mixture is heated to an internal temperature of 245° C in the course of 12 hours, after which the elimination of water has ended (33 parts of water). After removing excess amine and alcohol under reduced pressure, the N-(2'-phenylethyl)-1-naphthylamine distils at 225° - 230° C/5 mm Hg. 210 parts of N-(2'-phenylethyl)-1-naphthylamine (85% of theory) are obtained.

Workup

temperatureThe mixture is heated to an internal temperature of 245° C in the course of 12 hours
customAfter removing excess amine and alcohol under reduced pressure
customthe N-(2'-phenylethyl)-1-naphthylamine distils at 225° - 230° C/5 mm Hg

Sources & evidence

ORD record: ord-960cda7a4f08482f97ccb8b0c95f60df
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04067903

Reaction notes

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