Cyclohexene → 2-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide

HRID 1483966노트

반응식

HRID 1483966 반응식
[C:1]([C:3]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14])#[N:2].C1CCCCC=1>CCO.[Pd]>[NH2:22][C:21]1[C:3]([C:1]#[N:2])=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14]

참가 물질

5

반응물 2

HCID 8079CyclohexeneHCID 867142972-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide

생성물 1

HCID 867142962-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide수율 92.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (Example 26c, 0.458 g, 1.46 mmol) in EtOH (20 mL) was added cyclohexene (0.74 mL, 7.3 mmol) and catalytic amount of 10% Pd/C (0.146 mg). Reaction mixture was heated at 100° C. for 40 minutes, then filtered through Cellite, washed with EtOH (100 mL) and evaporated to give 2-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (0.407 g, 92%) which was used in to next step without further purification. MS 303 (MH+).

후처리

  1. customReaction mixture
  2. filtrationfiltered through Cellite
  3. washwashed with EtOH (100 mL)
  4. customevaporated

출처 및 근거

ORD 기록
ord-fa9d32aad2df429192ad01b6db564147
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09420814B2

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