2-Morpholinoethanol → (Z)-4-(1-(6-(2-morpholinoethoxy)pyridin-3-yl)-2-phenylbut-1-enyl)phenol

HRID 626102Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.Cl[C:11]1[N:16]=[CH:15][C:14](/[C:17](/[C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[C:18](\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH2:19][CH3:20])=[CH:13][CH:12]=1>>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:11]2[N:16]=[CH:15][C:14](/[C:17](/[C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)=[C:18](\[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)/[CH2:19][CH3:20])=[CH:13][CH:12]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 611632-Morpholinoethanol

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

Product 1

HCID 71600026(Z)-4-(1-(6-(2-morpholinoethoxy)pyridin-3-yl)-2-phenylbut-1-enyl)phenolYield 86%

Procedure

Following the same procedure as described in example 3, 2-morpholinoethanol (391 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 (110 mg, 86% yield). 1H NMR (400 MHz, CDCl3) δ 7.59 (s, 1H), 7.01-7.18 (m, 8H), 6.79 (d, J=8.8 Hz, 2H), 6.27 (d, J=8.4 Hz, 1H), 4.29 (t, J=5.6 Hz, 2H), 2.70 (t, J=5.6 Hz, 2H), 2.46-2.52 (m, 6H), 1.29-1.40 (m, 4H), 0.92 (t, J=7.6 Hz, 3H); m/z=431[M+1]+.

Sources & evidence

ORD record: ord-132ee672fefe49f78676c82f28cfd2de
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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