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

HRID 1785142ノート

反応式

HRID 1785142 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-396e9a3822ac41f887a958e235c64d18
出典データセット
uspto-grants-2009_03
特許番号
US07504408B2

反応ノート

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