Potassium Carbonate → N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403126ノート

反応式

HRID 403126 の反応式
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([O:17][C:18]1[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=1[CH2:20][N:21]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:22][CH2:23][CH2:24]Cl)([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:13]([O:17][C:18]1[CH:36]=[CH:35][CH:34]=[CH:33][C:19]=1[CH2:20][N:21]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH2:22][CH2:23][CH2:24][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)([CH3:14])([CH3:15])[CH3:16]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

生成物 1

HCID 70896369N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine収率 36%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-phenyl piperidin (0.21 g, 1.2 mmol), compound 19 (0.3 g, 0.86 mmol), KI (0.43 g, 2.59 mmol) and K2CO3 (0.59 g, 4.3 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 12 h. After cooling to room temperature, the inorganic salts were filtered, and the filtrate was evaporated to dryness. The residue was redissolved in CH2Cl2 and chromatographed on a silica gel TLC plate that was developed with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (36% yield). 1H NMR (CDCl3) δ 8.492 (dd, 1H, Ar), 7.619 (ddd, 1H, Ar), 7.571 (t, 2H, Ar), 7.272 (t, 2H, Ar), 7.203 (d, 2H, Ar), 7.167 (t, 1H, Ar), 7.107 (m, 2H, Ar), 7.024 (t, 2H, Ar), 3.770 (s, 2H, —CH2—), 3.695, (s, 2H, —CH2—), 3.003 (d, 2H, —CH2—), 2.524 (t, 2H, —CH2—), 2.459 (m, 1H, —CH—), 2.367 (t, 2H, —CH2—), 2.01 (ddd, 2H, —CH2—), 1.783 (m, 6H), 1.359 (s, 9H, —C(CH3)3). Mass Spec.=472.34 (M+H)+.

後処理

  1. temperaturethe solution was refluxed under argon atmosphere for 12 h
  2. filtrationthe inorganic salts were filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was redissolved in CH2Cl2
  5. customchromatographed on a silica gel TLC plate that

出典と根拠

ORDレコード
ord-65184d20557141c19de14d68d5c22d18
出典データセット
uspto-grants-2014_06
特許番号
US08747810B2

反応ノート

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