4-Amino-1-methylpiperidine → HCID 66716363, compound

HRID 2271575Notes

Reaction equation

HRID 2271575 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]([NH2:25])[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:25][CH:22]1[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66716363HCID 66716363, compoundYield 87%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (510 mg, 1.64 mmol) was reacted with 1-methylpiperidin-4-amine (375 mg, 3.28 mmol) to afford the desired product (552 mg, 87%) as a brown solid: 1H NMR (300 MHz, CD3OD) δ 9.12 (s, 1H), 8.38 (d, J=2.0 Hz, 1H), 7.84 (dd, J=8.9, 2.1 Hz, 1H), 7.79-7.71 (m, 1H), 4.20-3.97 (m, 1H), 2.93-2.69 (m, 3H), 2.47-2.19 (m, 5H), 2.19-2.03 (m, 2H), 1.86-1.60 (m, 2H), 1.32-1.16 (m, 2H), 1.16-1.00 (m, 2H).

Sources & evidence

ORD record
ord-45a1a7ee51fd4b82b00e03e7a625a4bd
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…