N,N-dimethyl-1-(piperidin-4-yl)ethanamine → (6-Bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone

HRID 2271577Notes

Reaction equation

HRID 2271577 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]([CH3:28])[CH:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:21]>>[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[N:25]1[CH2:26][CH2:27][CH:22]([CH:20]([N:19]([CH3:18])[CH3:28])[CH3:21])[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 23090463N,N-dimethyl-1-(piperidin-4-yl)ethanamineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 86692863(6-Bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanoneYield 63.6%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (300 mg, 0.965 mmol) was reacted with N,N-dimethyl-1-(piperidin-4-yl)ethanamine (332 mg, 1.45 mmol) to afford the desired product (264 mg, 63%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 8.78 (s, 1H), 8.32 (s, 1H), 7.95-7.80 (m, 2H), 3.57-3.39 (m, 2H), 3.21 3.05 (m, 2H), 2.59-2.42 (m, 2H), 2.31 (s, 6H), 2.11-1.97 (m, 1H), 1.89 (d, J=12.4 Hz, 1H), 1.80-1.67 (m, 1H), 1.68-1.49 (m, 2H), 1.36-1.16 (m, 4H), 1.06 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-3b59fa2ebd224a10bc1aa538e9545375
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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