Trifluoroacetic acid → 2,2-Dimethyl-1-(2-(methylsulfonyl)ethyl)piperazine

HRID 1945498Notes

Reaction equation

HRID 1945498 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]([CH3:21])([CH3:20])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][S:16]([CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C:10]1([CH3:21])[CH3:20])(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605798HCID 59605798, compound

Product 1

HCID 596060882,2-Dimethyl-1-(2-(methylsulfonyl)ethyl)piperazineYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-methanesulfonylethyl)-3,3-dimethylpiperazine-1-carboxylic acid tert-butyl ester (510 mg, 1.59 mmol) and TFA (5 mL) in DCM (10 mL) was stirred at room temperature for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording 1-(2-(Methanesulfonyl)ethyl)-2,2-dimethylpiperazine as a white solid (320 mg, 91%). 1H NMR (CDCl3, 300 MHz): δ 3.49 (s, 1 H); 3.12-3.03 (m, 5 H); 2.92-2.84 (m, 4 H); 2.60 (s, 2 H); 2.53-2.47 (m, 2 H); 1.06 (s, 6 H).

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-b1e9c1dc43cb4a4fa08d038240bb0caf
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…