tert-Butyl piperazine-1-carboxylate → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(piperazin-1-yl)ethoxy)phenyl)but-1-enyl)phenol

HRID 626266Notes

Reaction equation

HRID 626266 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.[N:32]1(C(OC(C)(C)C)=O)[CH2:37][CH2:36][NH: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:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)=[CH:17][CH:18]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804894-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(piperazin-1-yl)ethoxy)phenyl)but-1-enyl)phenol

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 tert-butyl piperazine-1-carboxylate (500 mg) in MeOH (3 mL) under reflux and separated via column chromatography, followed by treatment with 1 mL trifluoroacetic acid in 3 mL CH2Cl2 and then purified by column chromatography to give the desired product (Z/E=1/1) as a white solid. m/z=503[M+1]+.

Workup

  1. temperatureunder reflux
  2. customseparated via column chromatography
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-622bb7edf2ed44a29223fcaff7cfdfe0
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…