Reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([NH:16][C:17](=[O:31])[C:18]2[CH:23]=[C:22]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:21]=[C:20]([F:30])[CH:19]=2)=[CH:8][CH:7]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CCO>[F:30][C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:21]=1)[C:17]([NH:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:7][CH:8]=1)=[O:31]Participants
Procedure
A solution of N-[4-(3-chloropropoxy)-naphthalen-1-yl]-3-fluoro-5-piperidin-1-yl-benzamide (0.125 g, 0.283 mmol) and morpholine (0.123 g, 1.4 mmol) in EtOH (3 ml) is heated at 180° C. for 30 min by microwave. The mixture is then concentrated under vacuum and the residue purified by column chromatography on silica gel (5% MeOH in EtOAc) to give 3-fluoro-N-[4-(3-morpholin-4-yl-propoxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide as a white powder (90 mg, 64%). Mp: 70-72° C. 1H NMR (300 MHz, DMSO-d6) δ 10.23 (s, 1H), 8.23 (m, 1H), 7.86 (m, 1H), 7.56 (m, 2H), 7.45 (s, 1H), 7.42 (d, J=8.1, Hz, 1H), 7.16 (d, J=9.0 Hz, 1H), 7.01 (d, J=8.1Hz, 1H), 6.93 (s, 1H), 4.23 (t, J=6.3 Hz, 2H), 3.60 (t, J=4.5 Hz, 4H), 3.29 (m, 4H), 2.55 (m, 2H), 2.42 (bs, 4H), 2.04 (q, J=6.6 Hz, 2H), 1.60 (bs, 6H). MS: 492.4 (M+1).
Workup
- concentrationThe mixture is then concentrated under vacuum
- customthe residue purified by column chromatography on silica gel (5% MeOH in EtOAc)
Sources & evidence
- ORD record
- ord-80cd1e7b2cda460d9cebb8de2ff57416
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829560B2
Linked notes
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