4-(2-Morpholinoethoxy)naphthalen-1-amine → 3-Fluoro-N-[4-(2-morpholin-4-ylethoxy)-1-naphthyl]-5-piperidin-1-ylbenzamide

HRID 1641235Notes

Reaction equation

HRID 1641235 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:30]=1)[C:25](O)=[O:26]>>[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:30]=1)[C:25]([NH:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1)=[O:26]

Participants

3

Reactant 2

HCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amineHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Product 1

HCID 595532923-Fluoro-N-[4-(2-morpholin-4-ylethoxy)-1-naphthyl]-5-piperidin-1-ylbenzamide

Procedure

Compound is prepared from [4-(2-morpholin-4-ylethoxy)-1-naphthyl]amine (0.11 g, 0.40 mmol) and 3-fluoro-5-piperidin-1-ylbenzoic acid (0.10 g, 0.40 mmol) according to conditions described in general procedures E and F. A light pink solid is produced (67 mg). Mp: 150-151° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.60 (bs, 6H), 2.49-2.57 (m, 4H), 2.89 (bs, 2H), 3.30 (bs, 4H), 3.61 (bs, 4H), 4.32 (bs, 2H), 3.96 (d, J=12.6 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 7.15 (d, J=9.3 Hz, 1H), 7.40-7.45 (m, 2H), 7.54-7.57 (m, 2H), 7.83-7.87 (m, 1H), 8.23 (s, 1H), 10.24 (s, 1H); MS 478 (M+1).

Workup

  1. customA light pink solid is produced (67 mg)

Sources & evidence

ORD record
ord-b75a761081e94d37a418fc5f3753afa1
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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