Methyl 4-bromobenzoate → Methyl 4-(4-acetylpiperazin-1-yl)benzoate

HRID 1911356

반응식

HRID 1911356 반응식
[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]

참가 물질

6

반응물 4

HCID 12081Methyl 4-bromobenzoateHCID 62657Potassium Phosphate, TribasicHCID 837951-AcetylpiperazineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91f5f87cbe4d43c4b838f5aa7ebe5e19
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604022B2

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