Hydrochloric Acid → (S)-2-Isopropylpiperazine

HRID 16853Notes

Reaction equation

HRID 16853 reaction equation
[CH3:1][CH:2]([C@H:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1C(OC(C)(C)C)=O)[CH3:3].Cl>C(OCC)(=O)C.CO.O1CCOCC1>[CH3:1][CH:2]([C@H:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1)[CH3:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 17750439(2S)-2-Isopropylpiperazine, N1-BOC protected

Product 1

HCID 15023839(S)-2-IsopropylpiperazineYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (2S)-2-propan-2-ylpiperazine-1-carboxylate (2 g, 8.76 mmol) in a mixture of ethyl acetate (20 mL) and methanol (20.00 mL) was stirred at room temperature with 4M HCl in dioxane (30 mL) for 40 h under nitrogen. The reaction mixture was evaporated to dryness. The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 3.5M NH3/MeOH and pure fractions were evaporated to dryness to afford (2S)-2-propan-2-ylpiperazine (1.052 g, 94%) as a white solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customThe crude product was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-88f88e51d5eb4f599de4d1c9fcadaed2
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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