Potassium Carbonate → N-(2-((2-tert-butoxybenzyl)(3-(4-(2-methoxyphenyl)piperidin-1-yl)propyl)amino)ethyl)pivalamide
Reaction equation
[C:1]([O:5]C1C=CC=CC=1CN(CC1C=CC=CN=1)CCCN1CCC(C2C=CC=CC=2)CC1)(C)(C)C.CO[CH:38]1[CH2:43][CH:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:41][CH2:40][NH:39]1.[C:50]([O:54][C:55]1[CH:75]=[CH:74][CH:73]=[CH:72][C:56]=1[CH2:57][N:58]([CH2:68][CH2:69][CH2:70]Cl)[CH2:59][CH2:60][NH:61][C:62](=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:53])([CH3:52])[CH3:51].C([O-])([O-])=O.[K+].[K+]>>[C:50]([O:54][C:55]1[CH:75]=[CH:74][CH:73]=[CH:72][C:56]=1[CH2:57][N:58]([CH2:68][CH2:69][CH2:70][N:39]1[CH2:38][CH2:43][CH:42]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=2[O:5][CH3:1])[CH2:41][CH2:40]1)[CH2:59][CH2:60][NH:61][C:62](=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:53])([CH3:52])[CH3:51]Participants
Reactant 4
Product 1
Procedure
The same procedure as described for compound 20 was applied to 2-methoxy-4-phenyl piperidin (0.5 g, 2.63 mmol), compound 23 (0.7 g, 1.75 mmol), KI (0.87 g, 5.25 mmol) and K2CO3 (1.21 g, 8.75 mmol). The residue was purified on a silica gel TLC plate that was developed in 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (65% yield). 1H NMR (CDCl3) δ 7.3965 (m, 1H, Ar), 7.2067 (dd, 1H, Ar), 7.1655 (m, 1H, Ar), 7.1315 (m, 1H, Ar), 7.0245 (dd, 1H, Ar), 7.001 (s, 1H, Ar), 6.9195 (ddd, 1H, Ar), 6.8465 (s, 1H, Ar), 3.814 (s, 3H, —OCH3), 3.599, (s, 2H, —CH2—), 3.1885 (m, 2H, —CH2—), 3.041 (m, 2H, —CH2—), 2.951 (m, 1H, —CH—), 2.525 (t, 2H, —CH2—), 2.475 (t, 2H, —CH2—), 2.367 (t, 2H, —CH2—), 2.066 (m, 2H, —CH2—), 1.7455 (m, 6H), 1.430 (s, 9H, —C(CH3)3, 1.386 (s, 9H, —C(CH3)3. Mass Spec.=554.40 (M+H)+.
Workup
- customThe residue was purified on a silica gel TLC plate that
Sources & evidence
- ORD record
- ord-582fcf863f8e4776922a953e4c2b7796
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08747810B2
Reaction notes
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