Piperidine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)but-1-enyl)phenol

HRID 626260Notes

Reaction equation

HRID 626260 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.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]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:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:17][CH:18]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804694-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)but-1-enyl)phenolYield 82%

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 piperidine (1 mL) in MeOH (3 mL) under reflux to give the desired product (63 mg, 82%, Z/E=1/1) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.24 & 7.22 (s, 1H), 7.21 (d, J=9.2 Hz, 1H), 7.09 & 7.06 (d, J=8.6 Hz, 2H), 7.01 & 6.99 (d, J=8.8 Hz, 1H), 6.78 & 6.69 (d, J=8.2 Hz, 2H), 6.68 & 6.66 (d, J=8.6 Hz, 2H), 6.47 & 6.45 (s, 1H), 6.42 & 6.25 (d, J=8.6 Hz, 2H), 4.10 & 3.90 (t, J=6.0 Hz, 2H), 2.81 & 2.70 (t, J=6.0 Hz, 2H), 2.48-2.57 (m, 6H), 1.47-1.68 (m, 6H), 0.89-0.93 (m, 3H); m/z=502[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-3f1daaa9f2f4464ab85227b4abdf6235
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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