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

HRID 1785142노트

반응식

HRID 1785142 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-396e9a3822ac41f887a958e235c64d18
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504408B2

반응 노트

불러오는 중…