4-(2-Dimethylaminoethyl)aniline → HCID 118037107, compound

HRID 1508749Notes

Reaction equation

HRID 1508749 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[N:5]=[C:4]2[CH2:15][CH2:16][CH2:17][C:3]=12.[CH3:18][N:19]([CH3:29])[CH2:20][CH2:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>>[ClH:1].[Cl:14][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]3[CH2:15][CH2:16][CH2:17][C:3]3=[C:2]([NH:26][C:25]3[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][N:19]([CH3:18])[CH3:29])=[CH:28][CH:27]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 149398614-(2-Dimethylaminoethyl)anilineHCID 901106754-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 118037107HCID 118037107, compoundYield 73.8%

Procedure

Following general procedure B1, 4-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine (0.083 g, 0.31 mmol) was reacted with 4-(2-(dimethylamino)ethyl)aniline (0.062 g, 0.37 mmol), followed by formation of the hydrochloride salt to afford the title compound (0.098 g, 67%) as a light yellow solid. MW=464.86. 1H NMR (DMSO-d6, 500 MHz) δ 10.16 (s, 1H), 8.33 (s, 1H), 7.91-7.89 (m, 1H), 7.79-7.74 (m, 1H), 7.48-7.42 (m, 2H), 7.31-7.28 (m, 4H), 7.21 (s, 1H), 3.29-3.26 (m, 2H), 3.02-2.90 (m, 4H), 2.87-2.78 (m, 8H), 2.10 (quin, J=7.5 Hz, 2H); APCI MS m/z 392 [M+H]+.

Sources & evidence

ORD record
ord-aba3781ef98149b5bc4b9d31b3f55858
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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