1,1,1-Trifluoro-N-phenylmethanesulfonamide → 2-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridine

HRID 551585Notes

Reaction equation

HRID 551585 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11](OS(C(F)(F)F)(=O)=O)=[N:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:22]1([CH2:28][C:29]2N=CC(O)=[CH:31][CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1(NS(C(F)(F)F)(=O)=O)C=CC=CC=1>C(Cl)Cl>[NH3:1].[N:22]1([CH2:28][CH2:29][C:30]#[C:31][C:11]2[CH:10]=[CH:9][C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:13][N:12]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 445154576-Piperidin-1-ylmethyl-pyridin-3-olHCID 86074933Trifluoro-methanesulfonic acid 5-piperidin-1-ylmethyl-pyridin-2-yl ester

Product 2

HCID 222AmmoniaYield 0%HCID 115731942-(4-Piperidin-1-yl-but-1-ynyl)-5-piperidin-1-ylmethyl-pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoro-methanesulfonic acid 5-piperidin-1-ylmethyl-pyridin-2-yl ester. A solution of 6-piperidin-1-ylmethyl-pyridin-3-ol (0.225 g, 1.17 mmol), N-phenyltrifluoromethanesulfonamide (0.50 g, 1.41 mmol), and TEA (0.50 mL, 3.50 mmol) in DCM (20 mL) was heated at reflux for 18 h. The solvent was removed and chromatography of the residue (SiO2: 0-3% 2 M NH3 in MeOH/DCM) gave the title compound as a solid (0.036 g, 95%).

Workup

  1. temperatureat reflux for 18 h
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-bcad2d5f71c2400a9b2bc2b369c3a32d
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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