Hydrochloric Acid → 1-(3-Hydroxypropyl)piperazin-2-one

HRID 1785141Notes

Reaction equation

HRID 1785141 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]1=[O:25])(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][C:13]1=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68881505HCID 68881505, compound

Product 1

HCID 450885731-(3-Hydroxypropyl)piperazin-2-oneYield 57.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-3-oxopiperazine-1-carboxylate (2.90 g, 7.8 mmol) in 1,4-dioxane (10 ml) was treated at room temperature with a 4N solution of HCl in 1,4-dioxane (15 ml) and the resulting solution stirred 4 hr then evaporated. The residue was taken up in a 10% methanol in dichloromethane solution (30 ml) and basified with a 7N solution of ammonia in methanol then filtered and the filtrate evaporated. The residue was purified by column chromatography on silica using increasing concentrations of methanolic ammonia in dichloromethane as eluent to give 1-(3-hydroxypropyl)piperazin-2-one (708 mg, 57%) as a colourless oil; NMR Soectrum:(CDCl3) 1.77 (quintet, 2H), 2.72 (s(br), 2H), 3.09 (t, 2H), 3.32 (t, 2H), 3.55 (m, 6H).

Workup

  1. customthen evaporated
  2. filtrationthen filtered
  3. customthe filtrate evaporated
  4. customThe residue was purified by column chromatography on silica using
  5. temperatureincreasing concentrations of methanolic ammonia in dichloromethane as eluent

Sources & evidence

ORD record
ord-e1c1357707e24276ad6d34ac35b6ba18
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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