Potassium Carbonate → Tert-butyl 2-((2-tert-butoxybenzyl)(6-(4-phenylpiperidin-1-yl)hexyl)amino)ethylcarbamate

HRID 403122ノート

反応式

HRID 403122 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[C:31]1([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:27]([O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:40]1[CH2:41][CH2:42][CH:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:38][CH2:39]1)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:30])([CH3:29])[CH3:28]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 86672687Tert-butyl 2-((6-bromohexyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

生成物 1

HCID 70896342Tert-butyl 2-((2-tert-butoxybenzyl)(6-(4-phenylpiperidin-1-yl)hexyl)amino)ethylcarbamate収率 73%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The compound 15 (1.9 g, 4.46 mmol), 4-phenylpiperidine (1.128 g, 6.99 mmol) and K2CO3 (0.64 g, 4.66 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 16 h. After cooling to room temperature, the solvent was evaporated to dryness. Purification was carried out on a silica gel TLC plate that was developed in 3% methanolic NH3 (7 M NH3 in methanol)/97% CH2Cl2. The product was obtained as pale yellow oil (73%). 1H NMR (CDCl3) δ 7.382 (d, 1H, Ar), 7.289 (m, 2H, Ar), 7.229 (m, 2H, Ar), 7.186 (m, 1H, Ar), 7.136 (m, 1H, Ar), 7.013 (m, 2H, Ar), 3.587 (s, 2H, —CH2—), 3.160 (m, 2H, —CH2—), 3.071 (d, 2H, —CH2—), 2.519 (overlapping m, 2H, —CH2—), 2.496 (overlapping m, 1H, —CH—), 2.419 (t, 2H, —CH2—), 2.355 (m, 2H, —CH2—), 2.045 (m, 2H, —CH2—), 1.837 (m, 4H, —CH2—CH2—), 1.525 (m, 2H, —CH2—), 1.472 (m, 2H, —CH2—), 1.437 (s, 9H, —C(CH3)3), 1.426 (s, 9H, —C(CH3)3), 1.280 (m, 4H, —CH2—CH2—). Mass Spec=566.43 (M+H)+.

後処理

  1. temperaturethe solution was refluxed under argon atmosphere for 16 h
  2. customthe solvent was evaporated to dryness
  3. customPurification

出典と根拠

ORDレコード
ord-8b695ed372034ddabb23d54f8e3fae1b
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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