1-(2-Hydroxyethyl)-4-methylpiperazine → (Z)-4-(1-(6-(2-(4-methylpiperazin-1-yl)ethoxy)pyridin-3-yl)-2-phenyl but-1-enyl)phenol

HRID 626100Notes

Reaction equation

HRID 626100 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]1.Cl[C:12]1[N:17]=[CH:16][C:15](/[C:18](/[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[C:19](\[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)/[CH2:20][CH3:21])=[CH:14][CH:13]=1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:12]2[N:17]=[CH:16][C:15](/[C:18](/[C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)=[C:19](\[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)/[CH2:20][CH3:21])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 71617026(Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol

Product 1

HCID 71617255(Z)-4-(1-(6-(2-(4-methylpiperazin-1-yl)ethoxy)pyridin-3-yl)-2-phenyl but-1-enyl)phenolYield 121.1%

Procedure

Following the same procedure as described in example 3, 2-(4-methylpiperazin-1-yl)ethanol (430 mg, 10 eq) was reacted with (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (100 mg, 1 eq, prepared from example 1) to give the desired product (160 mg, 95% yield). 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 7.17-7.22 (m, 2H), 7.00-7.15 (m, 5H), 6.97 (d, J=8.0 Hz, 1H), 6.76 (d, J=8.8 Hz, 2H), 6.03 (d, J=8.8 Hz, 1H), 4.27 (t, J=5.6 Hz, 2H), 2.75 (t, J=5.6 Hz, 2H), 2.48-2.57 (m, 12H), 2.32 (s, 3H), 0.92 (t, J=7.6 Hz, 3H); m/z=444 [M+1]+.

Sources & evidence

ORD record
ord-933e798380c445d89da30aafb01aaa61
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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