1-Methylpiperazine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)but-1-enyl)phenol

HRID 626262Notes

Reaction equation

HRID 626262 reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21]Cl)=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:36]4[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]4)=[CH:17][CH:18]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804794-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)but-1-enyl)phenolYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (70 mg, 1.0 eq, made by example 11, step D) was reacted with 1-methylpiperazine (1 mL) in MeOH (8 mL) under reflux to give the desired product (60 mg, 76%, Z/E=1/1.7) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 1H), 7.20 (d, J=8.8 Hz, 1H), 7.12 & 7.08 (d, J=8.8 Hz, 2H), 7.00 (d, J=8.8 Hz, 1H), 6.83 & 6.78 (d, J=8.8 Hz, 2H), 6.72 & 6.69 (d, J=8.8 Hz, 2H), 6.45 & 6.44 (s, 1H), 6.42 (d, J=8.8 Hz, 2H), 4.12 & 3.93 (t, J=5.6 Hz, 2H), 2.84 & 2.73 (t, J=5.6 Hz, 2H), 2.40-2.62 (m, 10H), 2.31 & 2.82 (s, 3H), 0.91 (t, J=7.2 Hz, 3H); m/z=517[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-853bab58cf3d4b9987aa65193fff4797
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…