Benzyldiphenylamine → N,N-Diphenyl-1-naphthalenemethanamine

HRID 1197240Notes

Reaction equation

HRID 1197240 reaction equation
[CH2:1](OC1C=CC=CC=1)[C:2]1C=CC=[CH:4][CH:3]=1.[CH2:15]([N:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:29]1([N:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2[C:17]3[C:18](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:19]=[CH:20][CH:21]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 69080BenzyldiphenylamineHCID 70352Benzyl Phenyl Ether

Product 1

HCID 11088172N,N-Diphenyl-1-naphthalenemethanamineYield 74%

Procedure

N-phenylnaphthaldimine (2.20 g, 0.010 mol) and benzylphenyl ether (1.84 g, 0.010 mol) were reacted as above for the preparation of benzyldiphenylamine. Aqueous work-up afforded a precipitate which was isolated by filtration and recrystallized from 95% ethanol to yield 2.3 g (74%) of needles, mp 170°-172° C. Anal. calcd. for C23H19N: C 89.28, H 6.19, N 4.53%; found: C 89.11, H 6.26, N 4.44%. 1H NMR (200 MHz, CDCl3) δ(assignment): 5.52 (s, 2H, CH2), 7.00-8.10 (m, 17H, aromatic). MS [m/e (70 ev, % of base peak)](C10H7)CH2N(C6H5)2 309 (M+., 4.8), 308 (M+--H., 29.0), 168 (M+--((C10H7)CH2)., 18.0), 141 (((C10H7)CH2)+., 100 ). FTIR (CDCl3): 3063, 3040, 1606, 1602, 1594, 1584, 1574, 1559, 1512, 1501, 1497, 1488, 1485, 1474, 1465, 1460, 1451 cm-1.

Workup

  1. customAqueous work-up afforded a precipitate which
  2. customwas isolated by filtration
  3. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-c1c8896bfb714cee8eb6b193d13c5149
Source dataset
uspto-grants-1992_05
Patent number
US05117062

Reaction notes

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