Ammonia → (R)-6-(2-(2-methylpyrrolidin-1-yl)ethyl)-2-(4-(piperidin-1-yl)phenyl)quinoline

HRID 11333Notes

Reaction equation

HRID 11333 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][C:17]1[N:18]=[C:19]([C:25]2S[CH:27]=[CH:28][CH:29]=2)S[C:21]=1[C:22](=O)[CH3:23].[NH3:30]>>[CH3:16][C@@H:17]1[CH2:21][CH2:22][CH2:23][N:18]1[CH2:19][CH2:25][C:29]1[CH:9]=[C:10]2[C:13](=[CH:27][CH:28]=1)[N:30]=[C:13]([C:10]1[CH:11]=[CH:12][C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:8][CH:9]=1)[CH:14]=[CH:11]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 825614'-PiperidinoacetophenoneHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanone

Product 1

HCID 11524148(R)-6-(2-(2-methylpyrrolidin-1-yl)ethyl)-2-(4-(piperidin-1-yl)phenyl)quinoline

Procedure

The title compound was prepared using the procedure described in Example 1G using 1-(4-piperidin-1-yl-phenyl)-ethanone for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.14 (d, J=5.42 Hz, 3H), 1.70 (m, 10H), 2.24 (m, 1H), 2.39 (m, 2H), 3.01 (m, 2H), 3.14 (m, 1H), 3.29 (m, 5H), 7.04 (d, J=8.81 Hz, 2H), 7.56 (dd, J=8.48, 2.03 Hz, 1H), 7.59 (s, 1H), 7.80 (d, J=8.48 Hz, 1H), 8.01–8.10 (m, 4H); MS (DCI-NH3) [M+H]+ at 400.

Sources & evidence

ORD record
ord-0270a166b2234c0fbf846ad340ecf1ba
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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