4-(Dimethylaminomethyl)piperidine → (6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone

HRID 2271572Notes

Reaction equation

HRID 2271572 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]([CH3:27])[CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]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[N:24]1[CH2:25][CH2:26][CH:21]([CH2:20][N:19]([CH3:27])[CH3:18])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 111372684-(Dimethylaminomethyl)piperidineHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715711(6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanoneYield 56.5%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (211 mg, 0.680 mmol) was reacted with N,N-dimethyl-1-(piperidin-4-yl)methanamine (97 mg, 0.680 mmol) to afford the desired product (160 mg, 46%) as a yellow glass: ESI MS m/z 417 [C21H26BrN3O+H]+.

Sources & evidence

ORD record
ord-d18d1d710ebd4e8d9ae8922308ae4a5f
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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