1-[5-(Ethyloxy)-2-methyl-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine → 2-(Ethyloxy)-5-methyl-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline

HRID 419628ノート

反応式

HRID 419628 の反応式
[CH2:1]([O:3][C:4]1[C:5]([N+:23]([O-])=O)=[CH:6][C:7]([CH3:22])=[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)[CH:9]=1)[CH3:2]>CCOC(C)=O.CO.[Pt]>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:15]2)[C:7]([CH3:22])=[CH:6][C:5]=1[NH2:23])[CH3:2]

参加物

5

反応物 1

HCID 594525651-[5-(Ethyloxy)-2-methyl-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine

生成物 1

HCID 594527752-(Ethyloxy)-5-methyl-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline収率 90%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 1-[5-(ethyloxy)-2-methyl-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperidine (33.1 g, 89.0 mmol) in EtOAc (800 mL) and MeOH (200 mL) was added platinum on carbon (sulfided) (17.5 g, 4.47 mmol). The mixture was stirred under H2 (1 atm.) over the weekend. The mixture was filtered through Celite®, washed with DCM, and rotovapped down. The resultant solid was triturated with diethyl ether to provide the title compound of Step G (27.3 g, 80 mmol, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ 6.54 (s, 1H), 6.44 (s, 1H), 4.28 (s, 2H), 3.94 (q, J=6.9 Hz, 2H), 3.11-3.22 (m, 2H), 2.97 (s, 3H), 2.87 (d, J=11.5 Hz, 2H), 2.44-2.56 (m, 2H), 2.06 (s, 3H), 1.59-1.80 (m, 4H), 1.43 (ddd, J=14.2, 7.0, 3.5 Hz, 1H), 1.21-1.36 (m, 5H).

後処理

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with DCM
  3. customThe resultant solid was triturated with diethyl ether

出典と根拠

ORDレコード
ord-4d7b5df09c0c4765873f1ddae3e27be4
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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