Formaldehyde → 1-(3-Hydroxypropyl)-4-methylpiperazin-2-one

HRID 1785142Notes

Reaction equation

HRID 1785142 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][C:6]1=[O:11].[CH2:12]=O>C(O)=O>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:12])[CH2:7][C:6]1=[O:11]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 450885731-(3-Hydroxypropyl)piperazin-2-one

Product 1

HCID 450995871-(3-Hydroxypropyl)-4-methylpiperazin-2-oneYield 93%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-(3-Hydroxypropyl)piperazin-2-one (700 mg, 4.43 mmol) in formic acid (10 ml) and 37/40% aqueous formaldehyde solution (5 ml) was stirred and heated at 95° for 2 hr then the resulting solution evaporated in vacuo. The residue was taken up in 5% methanol in dichloromethane (20 ml), basified with a 7N solution of ammonia in methanol and stirred 4.5 hr at room temperature. The mixture was filtered and the filtrate purified by column chromatography on silica using increasing concentrations of methanolic ammonia in dichloromethane as eluent to give 1-(3-hydroxypropyl)-4-methylpiperazin-2-one (710 mg, 93%) as a colourless oil; NMR Spectrum:(CDCl3) 1.73 (quintet, 2H), 2.34 (s, 3H), 2.66 (t, 2H), 3.13 (s, 2H), 3.33 (t, 2H), 3.53 (m, 4H), 3.80 (s(broad, 1H).

Workup

  1. temperatureheated at 95° for 2 hr
  2. customthe resulting solution evaporated in vacuo
  3. filtrationThe mixture was filtered
  4. customthe filtrate purified by column chromatography on silica using
  5. temperatureincreasing concentrations of methanolic ammonia in dichloromethane as eluent

Sources & evidence

ORD record
ord-396e9a3822ac41f887a958e235c64d18
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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