碳酸钾 → Methyl 4-(4-propan-2-yl-piperazin-1-yl)benzoate

HRID 16777

反应方程式

HRID 16777 反应方程式
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[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.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>[CH3:2][CH: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)[CH3:3]

参与物

7

反应物 3

HCID 11430碳酸钾HCID 12081对溴苯甲酸甲酯HCID 780131-异丙基哌嗪

产物 1

HCID 69129778Methyl 4-(4-propan-2-yl-piperazin-1-yl)benzoate收率 64.8%

试剂、催化剂与溶剂 3

HCID 27342172-二环己膦基-2'-(N,N-二甲胺)-联苯催化剂HCID 9811564三(二亚苄基丙酮)二钯催化剂HCID 8071乙二醇二甲醚溶剂

反应条件

温度
130 °C

实验过程

Tris(dibenzylideneacetone)dipalladium(0) (0.014 g, 0.02 mmol) was added to a deoxygenated suspension of 1-isopropylpiperazine (0.151 g, 1.18 mmol), methyl 4-bromobenzoate (0.215 g, 1 mmol), potassium carbonate (0.193 g, 1.4 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.012 g, 0.03 mmol) in DME (4 mL), and sealed into a microwave tube. The reaction was heated to 130° C. for 10 mins in the microwave reactor and cooled to room temperature. The reaction mixture was evaporated to dryness, redissolved in EtOAc (25 mL) and washed sequentially with water (15 mL) and saturated brine (15 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by silica column chromatography, eluting with 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-propan-2-yl-piperizin-1-yl)benzoate (0.170 g, 64.8%) as a tan solid.

后处理

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionredissolved in EtOAc (25 mL)
  5. washwashed sequentially with water (15 mL) and saturated brine (15 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford crude product
  10. customThe crude product was purified by silica column chromatography
  11. washeluting with 5% MeOH in DCM
  12. customPure fractions were evaporated to dryness

来源与证据

ORD记录
ord-4f87b8ae39c644da980c51f4ff0bae70
来源数据集
uspto-grants-2010_06
专利号
US07737149B2

关联笔记

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