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

HRID 535653

反応式

HRID 535653 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
120 °C

実験手順

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; 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.

後処理

  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; DCM/MeOH; gradient 0-2%)

出典と根拠

ORDレコード
ord-fad5ab25af9f4a149521755b80ec1b68
出典データセット
uspto-grants-2014_10
特許番号
US08859534B2

関連ノート

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