Phenyl-1-naphthylamine → N,N'-Diphenyl-N,N'-di-1-naphthyl-2-butene-1,4-diamine

HRID 1974792Notes

Reaction equation

HRID 1974792 reaction equation
[C:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:19][CH:20]=[CH:21][CH2:22]Br>>[C:1]1([N:7]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:19][CH:20]=[CH:21][CH2:22][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7013Phenyl-1-naphthylamineHCID 131802-Butene, 1,4-dibromo-

Product 1

HCID 54159014N,N'-Diphenyl-N,N'-di-1-naphthyl-2-butene-1,4-diamineYield 17.5%

Conditions

Temperature
70 °C

Procedure

A mixture of N-phenyl-1-naphthylamine (63 g, 0.29 mol) and 1.4-dibromobut-2-ene (12 g, 0.056 mol) is heated to 70° C. for three days. The resulting reaction mass is allowed to cool and is then extracted with 3×100 ml of hot hexane. The combined hexane extracts are concentrated in vacuo to an oil which is chromatographed (silica gel. 95/5 cyclohexane/diethyl ether) to give an oil. Said oil is then crystallized from ether to give 4.8 g (17.5% yield) of the title compound as a tan solid melting at 140°-142° C.

Workup

  1. customThe resulting reaction mass
  2. temperatureto cool
  3. extractionis then extracted with 3×100 ml of hot hexane
  4. concentrationThe combined hexane extracts are concentrated in vacuo to an oil which
  5. customis chromatographed (silica gel. 95/5 cyclohexane/diethyl ether)
  6. customto give an oil
  7. customis then crystallized from ether

Sources & evidence

ORD record
ord-b098afa4704c408293b13ec78a15a585
Source dataset
uspto-grants-1994_02
Patent number
US05283367

Reaction notes

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