Potassium Carbonate → Tert-butyl 2-((3-(4-(2-methoxyphenyl)piperidin-1-yl)propyl)(pyridin-2-ylmethyl)amino)acetate
Reaction equation
C(OC1C=CC=CC=1[CH2:8][N:9]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:15][CH2:14]1)(C)(C)C.COC1[CH2:45][CH:44]([C:46]2C=CC=CC=2)[CH2:43]CN1.[C:52]([O-:55])([O-])=[O:53].[K+].[K+]>>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:8][C:52]([O:55][C:44]([CH3:46])([CH3:45])[CH3:43])=[O:53])[CH2:18][CH2:17]1Participants
Reactant 3
Product 1
Procedure
Using procedures similar to that used for compound 21, [×6] was synthesized with 2-methoxy-4-phenylpiperidin (0.36 g, 1.90 mmol), compound [X5] (0.38 g, 1.27 mmol), KI (0.63 g, 3.8 mmol) and K2CO3 (0.876 g, 6.35 mmol). Purification was carried out on a silica gel preparative plate that was developed in with a 1% methanolic NH3 (7 M NH3 in methanol/99% CH2Cl2. The product was isolated as pale yellow oil (66%). 1H NMR (CDCl3) δ 8.521 (dd, 1H, Ar), 7.643 (ddd, 1H, Ar), 7.528 (d, 1H, Ar), 7.193-7.126 (m, 3H, Ar), 6.910 (t, 1H, Ar), 6.860 (d, 1H, Ar), 3.921 (s, 2H, —CH2—), 3.906 (s, 3H, —OCH3), 3.309 (s, 2H, —CH2—), 3.039 (s(br), 2H, —CH2—), 2.943 (m, 1H, —CH—), 2.696 (t, 2H, —CH2—), 2.416 (s(br), 2H, —CH2—), 2.088 (s(br), 2H, —CH2—), 1.775 (m(br), 6H), 1.459 (s, 9H, —C(CH3)3).
Workup
- customPurification
Sources & evidence
- ORD record
- ord-d9cf9df00359487aa480bd06a3e84918
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08747810B2
Reaction notes
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