Hydrochloric Acid → (S)-2-Isopropylpiperazine

HRID 1092123Notes

Reaction equation

HRID 1092123 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-8f6fc2ef01c74219b481956de6612276
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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