Potassium Carbonate → HCID 71062035、化合物

HRID 1774316ノート

反応式

HRID 1774316 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:8].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31]2[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[O:8])[CH2:33][CH2:32]2)=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 220016181386927-90-7HCID 72545477HCID 72545477、化合物

生成物 1

HCID 71062035HCID 71062035、化合物収率 60%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A stirred mixture of 6-bromo-N-(2-pyridylmethyl)hexanamide (0.60 g, 2.1 mmol), 1-[2-(4-methoxyphenyl)phenyl]piperazine (0.68 g, 2.5 mmol) and K2CO3 (3.5 mmol) in acetonitrile was refluxed overnight. After cooling, the mixture was evaporated to dryness and H2O (20 mL) was added to the residue. The aqueous phase was extracted with AcOEt (2×30 mL). The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/MeOH, 19:1, as eluent) to afford pure compound in 60% yield. 1H NMR (CDCl3): δ 1.35-1.42 (m, 2H), 1.53-1.63 (m, 2H), 1.68-1.78 (m, 2H), 2.28 (t, 2H, J=7.4 Hz), 2.42 (app. t, 2H), 2.65 (br s, 4H), 3.09 (br s, 4H), 3.81 (s, 3H), 4.45 (d, 2H, J=6.1 Hz), 6.12 (br t, 1H, D2O exchanged), 6.94 (d, 2H, J=8.8 Hz), 7.00 (d, 1H, J=8.0 Hz), 7.09-7.16 (m, 2H), 7.22-7.30 (m, 3H), 7.46 (d, 2H, J=8.8 Hz), 8.58 (m, 1H). GC-MS m/z 473 (M+1, 1), 472 (M+, 5), 379 (20), 282 (50), 226 (100), 210 (35).

後処理

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness and H2O (20 mL)
  4. additionwas added to the residue
  5. extractionThe aqueous phase was extracted with AcOEt (2×30 mL)
  6. dry with materialThe collected organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude residue was chromatographed (CHCl3/MeOH, 19:1, as eluent)
  9. customto afford pure compound in 60% yield

出典と根拠

ORDレコード
ord-c1ab2663133049b088c8ed2233b584bc
出典データセット
uspto-grants-2016_02
特許番号
US09260400B2

反応ノート

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