4-[(10-benzyl-9,10-diazatricyclo-[4.2.1.12,5]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide → 4-[(2,7-diazatricyclo[4.4.0.03,8]dec-2-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide
Reaction equation
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(N1C2C3N(C(C4C=CC=C(OC)C=4)C4C=CC(C(N(CC)CC)=O)=CC=4)C(CC2)C1CC3)C1C=CC=CC=1>>[CH:13]12[CH2:11][CH2:10][CH:9]3[CH:16]([CH2:15][CH2:14][CH:12]1[NH:8]3)[N:17]2[CH:18]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=1)[C:19]1[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])=[O:24])=[CH:21][CH:20]=1Participants
3
Reactant 2
Product 1
Procedure
The same procedure of Example 5.1 was repeated, but using instead of the compound prepared in Example 4.1 the compound 4-[(7-benzyl-2,7-diazatricyclo[4.4.0.03,8]dec-2-yl)-(3-methoxy-phenyl)methyl]-N,N-diethyl benzamide of Example 4.5. The compound 4-[(2,7-diazatricyclo[4.4.0.03,8]dec-2-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide was obtained. Yield: 90%. IR (nujol) (λ=cm−1) 1670 (C═O), 3100 (NH); 1H-NMR (CDCl3) δ 1.00-1.40 (m, 6H); 1.90-2.50 (m, 10H); 2.90-3.00 (m, 2H); 3.10-3.30 (m, 2H); 3.40-3.60 (m, 2H); 3.96 (s, 3H); 4.95 (s, 1H); 6.65-6.85 (m, 1H); 7.00-7.40 (m, 5H); 7.48 (d, 2H, J=6.0 Hz). Anal. calc. for C27H35N3O2: C, 74.79; H, 8.14; N, 9.69. Found: C, 74.81; H, 8.11; N, 9.68.
Sources & evidence
- ORD record
- ord-6eeb081f12d242fc92848bfa2ce4afef
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609659B2
Reaction notes
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