1-Methylpiperidine-4-methylamine → HCID 66715958, compound

HRID 2271578Notes

Reaction equation

HRID 2271578 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2Cl.[CH3:18][N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH2:26])[CH2:21][CH2:20]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 815741-Methylpiperidine-4-methylamineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715958HCID 66715958, compoundYield 85.2%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (0.880 g, 2.83 mmol) was reacted with (1-methylpiperidin-4-yl)methanamine (435 mg, 3.39 mmol) to afford the desired product (970 mg, 85%) as a light brown solid: 1H NMR (300 MHz, CDCl3) δ 10.87 (s, 1H), 9.22 (s, 1H), 8.36 (d, J=1.9 Hz, 1H), 7.80 (d, J=8.9 Hz, 1H), 7.73 (dd, J=8.9, 2.0 Hz, 1H), 3.69 (dd, J=6.4, 5.2 Hz, 2H), 2.93 (d, J=11.4 Hz, 2H), 2.79-2.60 (m, 1H), 2.31 (s, J=9.0 Hz, 3H), 2.01 (t, J=11.7 Hz, 2H), 1.89 (d, J=12.7 Hz, 2H), 1.76-1.60 (m, 1H), 1.53-1.30 (m, 2H), 1.30-1.17 (m, 2H), 1.10-0.95 (m, 2H).

Sources & evidence

ORD record
ord-b8410c49246e4dc8a823c0d2fbcbb2e5
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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