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Potassium Carbonate → 1-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)-methyl]-N-[bis(4-fluorophenyl)methyl]-4-piperidinamine

HRID 565705
ノート
印刷プレビュー

反応式

HRID 565705 の反応式
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O>[NH2:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]2[O:4][C:3]([CH2:2][N:29]3[CH2:30][CH2:31][CH:26]([NH:25][CH:24]([C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=4)[C:32]4[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=4)[CH2:27][CH2:28]3)([CH3:16])[CH2:7][C:6]=2[C:8]=1[CH3:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamineHCID 22111003N-[Bis(4-fluorophenyl)methyl]piperidin-4-amine

生成物 1

HCID 221111031-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)-methyl]-N-[bis(4-fluorophenyl)methyl]-4-piperidinamine収率 39%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 31374Dimethylacetamide溶媒

反応条件

温度
172 °C

実験手順

Under argon gas, a suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g), N-[bis(4-fluorophenyl)methyl]-4-piperidinamine (4.5 g), and potassium carbonate (1.4 g) in N,N-dimethylacetamide (20 mL) was stirred at 172° C. for 4.5 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatograph (silica gel/ethyl acetate and basic silica gel/hexane:ethyl acetate=9:1-85:15) and recrystallized from ethyl acetate-hexane to provide the title compound (0.97 g, yield 39%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatograph (silica gel/ethyl acetate and basic silica gel/hexane:ethyl acetate=9:1-85:15)
  6. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-54304349fe7b45a5905c75eff1849536
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06172085B2

反応ノート

読み込み中…

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