Trifluoroacetic acid → 4-(Azetidin-3-yl)piperazin-2-one

HRID 1945510Notes

Reaction equation

HRID 1945510 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596054391-Boc-3-(3-oxo-1-piperazinyl)azetidine

Product 1

HCID 596061454-(Azetidin-3-yl)piperazin-2-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-oxopiperazin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (400 mg, 1.57 mmol) and TFA (3 mL) in DCM (6 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 4-Azetidin-3-ylpiperazin-2-one as a white solid (227 mg, 93%). 1H NMR (CDCl3, 300 MHz): δ 6.08 (s, 1 H); 3.63-3.56 (m, 3 H); 3.42-3.35 (m, 3 H); 3.31 (t, J=6.74 Hz, 1 H); 3.03 (s, 2 H); 2.59-2.51 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-cf6e9c47763d4303bebab6c5a193ff0b
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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