O-Phenylenediamine → N,N-bis(1-H-benzimidazol-2-ylmethyl)-N-(3-phenyl)propylamine

HRID 1645200Notes

Reaction equation

HRID 1645200 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]1([CH2:15][CH2:16][CH2:17][N:18]([CH2:23][C:24](O)=O)[CH2:19][C:20](O)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)CO>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:20]1[CH2:19][N:18]([CH2:23][C:24]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH2:17][CH2:16][CH2:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 7470062-[Carboxymethyl(3-phenylpropyl)amino]acetic acid

Product 1

HCID 86638458N,N-bis(1-H-benzimidazol-2-ylmethyl)-N-(3-phenyl)propylamine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

2c was synthesised by an analogous procedure to that described for 2a using o-phenylenediamine (4.32 g, 40 mmol) and N-(3-phenyl)propyliminodiacetic acid (5 g, 20 mmol) in ethyleneglycol (10 ml) at 190° C. Yield 6.9 g (84%). 1H NMR (400.13 MHz, CD3OD, r.t.), δ 1.74 (quintet, 2H, CH2), 2.45 (m, 4H, CH2), 3.95 (s, 4H, NCH2), 6.88 (d, 2H, ArH), 6.94-6.95 (dd, 3H, ArH), 7.21 (m, 4H, ArH), 7.56 (m, 4H, ArH), 12.33 (broad s, 1.5H, NH). 13C NMR (100.6 MHz, MeOH-d4, r.t.), δ 29.49 (CH2), 34.04 (CH2), 53.95 (2 x NCH2) 55.13 (NCH2), 115.47 (broad, ArC), 123.59 (ArC), 126.58 (ArC), 129.09 (ArC), 129.24 (ArC), 142.95 (ArCq), 154.22 (ArCq from imidazole ring). Anal. Calc. for C25H25N5 (in %) C, 75.54; H, 6.85; N, 17.62. Found C, 75.88; H, 6.55; N, 17.65. +CI MS: (m/z): 396 ([MH+]), 280 ([M-CH2Ph]+).

Workup

  1. customat 190° C

Sources & evidence

ORD record
ord-abfed58cf8da4c06b02155a53d887a8d
Source dataset
uspto-grants-2012_02
Patent number
US08124698B2

Reaction notes

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