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

HRID 1092047

반응식

HRID 1092047 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f048eb6a13a84914a2cb66b95d938966
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129391B2

연결된 노트

불러오는 중…