N,N-dimethyl-1-(piperidin-4-yl)ethanamine → 1-{1-[6-Bromo-3-(methylsulfonyl)quinolin-4-yl]piperidin-4-yl}-N,N-dimethylethanamine

HRID 2271591Notes

Reaction equation

HRID 2271591 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]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2Cl.[CH3:17][N:18]([CH3:27])[CH:19]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[N:24]1[CH2:25][CH2:26][CH:21]([CH:19]([N:18]([CH3:17])[CH3:27])[CH3:20])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 23090463N,N-dimethyl-1-(piperidin-4-yl)ethanamineHCID 667152456-Bromo-4-chloro-3-(methylsulfonyl)quinoline

Product 1

HCID 667152671-{1-[6-Bromo-3-(methylsulfonyl)quinolin-4-yl]piperidin-4-yl}-N,N-dimethylethanamineYield 68%

Procedure

Following general procedure B, 6-bromo-4-chloro-3-(methylsulfonyl)quinoline (100 mg, 0.311 mmol) was reacted with N,N-dimethyl-1-(piperidin-4-yl)ethanamine (229 mg, 1.00 mmol) to afford the desired product (93 mg, 68%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 9.24 (s, 1H), 8.50 (d, J=1.5 Hz, 1H), 8.11-7.93 (m, 2H), 3.67-3.55 (m, 2H), 3.44 (s, 3H), 3.34 (s, 2H), 2.75-2.62 (m, 1H), 2.46 (s, 6H), 2.07-1.96 (m, 1H), 1.90 (d, J=12.3 Hz, 2H), 1.73-1.53 (m, 2H), 1.15 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-81732d38720a4d6793ebd50b2b7924b4
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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