Dimethylamine → 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide

HRID 383825

반응식

HRID 383825 반응식
C([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=O)C.C[Al](C)C.C[Al](C)C.C1N2CC[N:38]([CH2:39]C2)[CH2:37]1.CNC>O1CCCC1.[Cl-].[Na+].O>[CH2:21]([N:18]1[CH2:17][CH2:16][N:15]([C:14]2[C:8]3[O:7][C:6]([C:4]([N:38]([CH3:39])[CH3:37])=[O:3])=[CH:10][C:9]=3[CH:11]=[CH:12][CH:13]=2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 3

HCID 674DimethylamineHCID 166883661,4-Diazabicyclo(2.2.2)octane--trimethylalumane (1/2)HCID 596367457-(4-Benzyl-piperazin-1-yl)-benzofuran-2-carboxylic acid ethyl ester

생성물 1

HCID 596367707-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide수율 87.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
120 °C

실험 절차

7-(4-Benzyl-piperazin-1-yl)-benzofuran-2-carboxylic acid ethyl ester (1.0 g, 2.74 mmol) and DABAL-Me3 (0.56 g, 2.20 mmol) were mixed in tetrahydrofuran (5 mL). Dimethylamine (2M in THF) (2.2 mL, 4.39 mmol) was added and the mixture was heated by microwave irradiation to 120° C. for 15 min. Brine was added and the mixture was extracted with dichloromethane, dried over Na2SO4, filtered and the solvent removed by rotary evaporation. The product was purified by flash chromatography (SiO2; to DCM/MeOH; gradient 0-2%) giving 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide (0.70 g, 1.93 mmol) in 70% yield.

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed by rotary evaporation
  5. customThe product was purified by flash chromatography (SiO2; to DCM/MeOH; gradient 0-2%)

출처 및 근거

ORD 기록
ord-7ecdbf52ef48430799ea9f2a5d938b07
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367676B2

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