N-Piperidinoethanol → (Z)-4-(2-phenyl-1-(6-(2-(piperidin-1-yl)ethoxy)pyridin-3-yl)but-1-enyl)phenol

HRID 626101Notes

Reaction equation

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

Participants

Reactant 2

HCID 18232N-Piperidinoethanol

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

Product 1

HCID 71617256(Z)-4-(2-phenyl-1-(6-(2-(piperidin-1-yl)ethoxy)pyridin-3-yl)but-1-enyl)phenolYield 83.1%

Procedure

Following the same procedure as described in example 3, 2-(piperidin-1-yl)ethanol (385 mg, 10 eq) was reacted with (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenyl but-1-enyl)phenol (100 mg, 1 eq, prepared from example 1) to give the desired product (106 mg, 83% yield). 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.16-7.21 (m, 2H), 7.01-7.15 (m, 6H), 6.88 (d, J=8.8 Hz, 1H), 6.77 (d, J=8.8 Hz, 2H), 5.63 (d, J=8.0 Hz, 1H), 4.25 (t, J=5.6 Hz, 2H), 2.73 (t, J=5.6 Hz, 2H), 2.40-2.62 (m, 6H), 1.63-1.75 (m, 4H), 1.44-1.56 (m, 2H), 0.92 (t, J=7.2 Hz, 3H); m/z=429 [M+1]+.

Sources & evidence

ORD record: ord-85e8dc570f0d4657ba151c95e2a9de7a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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