2-Chloro-5-phenylpyrimidine → N-[1-(3,4-dichlorobenzy)-4-piperidinyl]-N'-(5-phenyl-2-pyrimidinyl)-1,2-ethandiamine

HRID 1070524Notes

Reaction equation

HRID 1070524 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH2:7]1.Cl[C:21]1[N:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][N:22]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH2:13][CH2:14][NH:15][C:21]2[N:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][N:26]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6053202-Chloro-5-phenylpyrimidineHCID 10201974n1-[1-(3,4-Dichlorobenzyl)-4-piperidinyl]-1,2-ethanediamine

Product 1

HCID 20794189N-[1-(3,4-dichlorobenzy)-4-piperidinyl]-N'-(5-phenyl-2-pyrimidinyl)-1,2-ethandiamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound (20 mg) was prepared by heating at reflux N1-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-1,2-ethanediamine (100 mg) and 2-chloro-5-phenypyrimidine (100 mg) and Hunigs' base (100 mg) in toluene for 8 hours. The mixture was purified by chromatography on silica, with ethyl acetate methanol (9:1) as eluant to give the title compound as a yellow oil. MS [M+h]+ (ES+) 456/8 1H NMR: (CDCl3) δ 1.51 (2H, m), 1.75 (2H, m), 2.15 (2H, td), 2.9 (2H, m), 3.05 (1H, m), 3.15 (2H, m), 3.44 (2H, m), 3.8 (2H, m), 6.65 (1H, m), 7.0-7.4 (8H, m), 8.5 (2H, m).

Workup

  1. customThe title compound (20 mg) was prepared
  2. temperatureby heating
  3. customThe mixture was purified by chromatography on silica, with ethyl acetate methanol (9:1) as eluant

Sources & evidence

ORD record
ord-fb27f267493d47ccb4b3b4170edcbd33
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

Loading…