对溴苯甲酸甲酯 → Methyl 4-(4-acetylpiperazin-1-yl)benzoate

HRID 16785

反应方程式

HRID 16785 反应方程式
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参与物

6

反应物 4

HCID 12081对溴苯甲酸甲酯HCID 62657POTASSIUM DIPHOSPHATEHCID 837951-乙酰哌嗪HCID 112698722-双环己基膦-2',6'-二甲氧基联苯

产物 1

HCID 57440409Methyl 4-(4-acetylpiperazin-1-yl)benzoate收率 56.2%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

反应条件

温度
100 °C

实验过程

A deoxygenated suspension of 1-acetylpiperazine (0.308 g, 2.40 mmol), methyl 4-bromobenzoate (0.430 g, 2 mmol), tri-potassium orthophosphate (0.594 g, 2.80 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.164 g, 0.40 mmol) and tris(dibenzylideneacetone)dipaladium(0) (0.092 g, 0.10 mmol) in toluene (10 mL) was stirred at 100° C., over a period of 24 h under nitrogen. The cooled reaction mixture was filtered and evaporated to give crude product. The crude product was purified by silica column chromatography, eluting with a gradient 0-5% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-acetylpiperazin-1-yl)benzoate (0.295 g, 56.2%) as a yellow solid.

后处理

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customevaporated
  4. customto give crude product
  5. customThe crude product was purified by silica column chromatography
  6. washeluting with a gradient 0-5% MeOH in DCM
  7. customPure fractions were evaporated to dryness

来源与证据

ORD记录
ord-743a010bd61e44b484bd996ac6892806
来源数据集
uspto-grants-2010_06
专利号
US07737149B2

关联笔记

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