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

HRID 403122노트

반응식

HRID 403122 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-8b695ed372034ddabb23d54f8e3fae1b
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08747810B2

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