4-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide → 4-[(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxy phenyl)methyl]-N,N-diethylbenzamide

HRID 1912343노트

반응식

HRID 1912343 반응식
C([N:8]1[CH:12]2[CH:13]3[N:17]([CH:18]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)[C:19]4[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=4)[CH:16]([CH:9]1[CH2:10][CH2:11]2)[CH2:15][CH2:14]3)C1C=CC=CC=1>C(O)C.[Pd]>[CH:13]12[N:17]([CH:18]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)[C:19]3[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH:16]([CH2:15][CH2:14]1)[CH:9]1[NH:8][CH:12]2[CH2:11][CH2:10]1

참가 물질

4

반응물 1

HCID 672383574-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

생성물 1

HCID 672375014-[(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxy phenyl)methyl]-N,N-diethylbenzamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

0.38 mmoles of the compound 4-[(10-benzyl-9,10-diazatricyclo[4.2.1.12,5]-dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide obtained in Example 4.1 were mixed with palladium at 10% by weight on carbon (0.1 equivalents) in ethanol (5 ml). The mixture was submitted to hydrogenation at a pressure of 45 psi of H2 and at a temperature of 60° C., for 6 hours. At the end of the reaction the catalyst was removed by filtration under vacuum. The solvent was then evaporated under vacuum obtaining the compound 4-[(9,10-diazatricyclo[4.2.1.12,5]dec-9-yl)-(3-methoxy phenyl)methyl]-N,N-diethylbenzamide. Yield: quantitative. IR (nujol) (λ=cm−1) 1630 (C═O), 3200 (NH); 1H-NMR (CDCl3) δ 1.00-1.45 (m, 6H); 1.90-2.43 (m, 10H); 2.90-3.10 (m, 2H); 3.10-3.30 (m, 2H); 3.40-3.60 (m, 2H); 3.66 (bs, 1H); 3.79 (s, 3H); 4.26 (s, 1H); 6.75-6.80 (m, 1H); 7.03-7.38 (m, 5H); 7.60 (d, 2H, J=8.0 Hz). Anal. calc. for C27H35N3O2: C, 74.79; H, 8.14; N, 9.69. Found: C, 75.04; H, 8.13; N, 9.67.

후처리

  1. customAt the end of the reaction the catalyst
  2. customwas removed by filtration under vacuum
  3. customThe solvent was then evaporated under vacuum

출처 및 근거

ORD 기록
ord-9b6dba9262e14d11b618358bb52d0559
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609659B2

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