Potassium Carbonate → Methyl 4-(4-propan-2-yl-piperazin-1-yl)benzoate

HRID 1092047

反応式

HRID 1092047 の反応式
[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]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 12081Methyl 4-bromobenzoateHCID 780131-Isopropylpiperazine

生成物 1

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

試薬・触媒・溶媒 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f048eb6a13a84914a2cb66b95d938966
出典データセット
uspto-grants-2012_03
特許番号
US08129391B2

関連ノート

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