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

HRID 1092064

반응식

HRID 1092064 반응식
[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

참가 물질

6

반응물 2

HCID 167693Trimethylsilyldiazomethane2회HCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acid

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d95eaf64740474096573688ff61119a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129391B2

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