Acetonitrile → N-(2-tert-butoxybenzyl)-6-(4-(2-methoxyphenyl)cyclohexyl)-N-(pyridin-2-ylmethyl)hexan-1-amine

HRID 403117ノート

反応式

HRID 403117 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CO[CH:30]1[CH2:35][CH:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:33][CH2:32]N1.[C:42]([O-:45])([O-])=O.[K+].[K+].[CH3:48]C#N>>[C:24]([O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH:39]1[CH2:38][CH2:37][CH:36]([C:34]2[CH:33]=[CH:32][CH:48]=[CH:30][C:35]=2[O:45][CH3:42])[CH2:41][CH2:40]1)([CH3:27])([CH3:26])[CH3:25]

参加物

5

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 671282442-Methoxy-4-phenylpiperidineHCID 866726866-bromo-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)hexan-1-amine

生成物 1

HCID 49850513N-(2-tert-butoxybenzyl)-6-(4-(2-methoxyphenyl)cyclohexyl)-N-(pyridin-2-ylmethyl)hexan-1-amine収率 58%

実験手順

The compound 10 (0.377 g, 0.85 mmol), 2-methoxy-4-phenylpiperidine (0.262 g, 1.54 mmol) and K2CO3 (0.118 g, 0.85 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 6 h and stirred overnight. Then the solvent was evaporated to dryness. Purification was carried out on a silica gel TLC plate that was developed in 4% methanolic NH3 (7 M NH3 in methanol)/96% CH2Cl2. The product was obtained as pale yellow oil (58%). 1H NMR (CDCl3) δ 8.491 (d, 1H, Ar), 7.262 (m, 1H, Ar), 7.583 (m, 2H, Ar), 7.216 (d, 1H, Ar), 7.160 (m, 1H, Ar), 7.112 (m, 2H, Ar), 7.024 (m, 2H, Ar), 6.917 (t, 1H, Ar), 6.839 (d, 1H, Ar), 3.806 (s, 3H, —OCH3), 3.744 (s, 2H, —CH2—), 3.667 (s, 2H, —CH2—), 3.043 (d, 2H, —CH2—), 2.958 (m, 1H, —CH—), 2.459 (t, 2H, —CH2—), 2.326 (m, 2H, —CH2—), 2.061 (m, 2H, —CH2—), 1.790 (m, 4H, —CH2—CH2—), 1.531 (m, 4H, —CH2—CH2—), 1.360 (s, 9H, —C(CH3)3—), 1.298 (m, 2H, —CH2—), 1.228 (m, 2H, —CH2—). Mass Spec.=543.78 (M+H)+.

後処理

  1. temperaturethe solution was refluxed under argon atmosphere for 6 h
  2. customThen the solvent was evaporated to dryness
  3. customPurification

出典と根拠

ORDレコード
ord-8bceeb1c7350482e8ae5f3fd694f4063
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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