Trifluoroacetic acid → (2S)-2-(4-Methoxybutyl)piperazine

HRID 131414Notes

Reaction equation

HRID 131414 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C@@H:9]1[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:26][O:25][CH2:24][CH2:23][CH2:22][CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58625892(S)-2-(4-Methoxybutyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 45099588(2S)-2-(4-Methoxybutyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a stirred, room temperature solution of (S)-2-(4-methoxybutyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.198 g, 0.53 mmol) in CH2Cl2 (2.6 mL), add TFA (2.6 mL) and stir for 2 h. Concentrate the mixture under reduced pressure, dilute with H2O and load onto an SCX column (10 g). Wash the resin with H2O (3×100 mL), MeOH (3×100 mL) and elute the product with 2 M NH3 in MeOH (3×100 mL). Concentrate the purified fractions under reduced pressure and azeotrope the residue with CH2Cl2/hexanes (1:2). Place the residue under vacuum to give the title compound: orange crystals (0.093 g), mass spectrum (m/e):173.4 (M+H).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. additiondilute with H2O and load onto an SCX column (10 g)
  3. washWash the resin with H2O (3×100 mL), MeOH (3×100 mL)
  4. washelute the product with 2 M NH3 in MeOH (3×100 mL)
  5. concentrationConcentrate the purified fractions under reduced pressure

Sources & evidence

ORD record
ord-7a0edb1d2f96414490800c2dca4d75ef
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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