Trimethylsilyldiazomethane → Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

HRID 16794ノート

反応式

HRID 16794 の反応式
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1>C1(C)C=CC=CC=1.CO.C(Cl)Cl>[CH3:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH3:1])=[O:21])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

参加物

6

反応物 2

HCID 167693Trimethylsilyldiazomethane2 回HCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acid

生成物 1

HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate収率 44.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (trimethylsilyl)diazomethane ((0.611 mL, 3.84 mmol) 2.0M in diethyl ether) was added dropwise to a stirred suspension of 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (0.75 g, 3.20 mmol) in toluene (21 mL) and methanol (7 mL) over a period of 10 mins under nitrogen. The resulting suspension was stirred at room temperature for 3 h. A further aliquot of (trimethylsilyl)diazomethane (1.222 mL, 7.68 mmol) was added dropwise and the solution was stirred at room temperature for a further 18 h. The reaction mixture was evaporated to dryness to afford the crude product (0.723 g) as a white solid. This was taken up in DCM and the insolubles were filtered off. The filtrate was evaporated to dryness to afford the crude product. This was taken up in DCM again and more insolubles were filtered off to afford methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate (0.351 g, 44.2%), which was used without purification.

後処理

  1. stirringthe solution was stirred at room temperature for a further 18 h
  2. customThe reaction mixture was evaporated to dryness
  3. customto afford the crude product (0.723 g) as a white solid
  4. filtrationthe insolubles were filtered off
  5. customThe filtrate was evaporated to dryness
  6. customto afford the crude product
  7. filtrationmore insolubles were filtered off

出典と根拠

ORDレコード
ord-37f83163a3964c7e86f2f9cd86e5db68
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

反応ノート

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