Pyridine → Methyl 4-(4-methylpiperazine-1-carbonyl)benzoate

HRID 16775

反応式

HRID 16775 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:10].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:15]([C:14]2[CH:13]=[CH:12][C:11]([C:9]([O:8][CH3:7])=[O:10])=[CH:19][CH:18]=2)=[O:17])[CH2:23][CH2:22]1

参加物

7

反応物 4

HCID 1049PyridineHCID 15513Monomethyl terephthalateHCID 531671-MethylpiperazineHCID 65578Oxalyl chloride

生成物 1

HCID 17178223Methyl 4-(4-methylpiperazine-1-carbonyl)benzoate収率 67.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

Oxalyl chloride (0.533 mL, 6.11 mmol) was added dropwise to a stirred suspension of 4-(methoxycarbonyl)benzoic acid (1 g, 5.55 mmol) in DCM (20 mL) under nitrogen. The resulting suspension was stirred at room temperature for 30 mins. DMF (0.05 mL) was added dropwise under nitrogen. The resulting suspension was stirred for 90 mins. A solution of 1-methylpiperazine (0.554 mL, 5.00 mmol) and pyridine (1.211 mL, 14.99 mmol) in DCM (15 mL) was added dropwise at 0° C., over a period of 60 mins under nitrogen. The resulting solution was stirred at room temperature for 3 h. The reaction mixture was evaporated to dryness to afford the crude product (1.791 g) as a dark orange solid. The solid was redissolved in DCM and washed with NaHCO3. The organic layer was evaporated to dryness to afford methyl 4-(4-methylpiperazine-1-carbonyl)benzoate (0.890 g, 61.1%) as an orange gum, which solidified on standing. Used without further purification.

後処理

  1. stirringThe resulting suspension was stirred for 90 mins
  2. stirringThe resulting solution was stirred at room temperature for 3 h
  3. customThe reaction mixture was evaporated to dryness
  4. customto afford the crude product (1.791 g) as a dark orange solid
  5. washwashed with NaHCO3
  6. customThe organic layer was evaporated to dryness

出典と根拠

ORDレコード
ord-fb35064d694440779fad2aeb07bf3334
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

関連ノート

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