4-(5-chloro-[1H]-indol-3-yl)-piperidine → HCID 131724872, compound

HRID 2180950Notes

Reaction equation

HRID 2180950 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][N:15](CCCC(N2C3C(=CC=CC=3)CCC2)=O)[CH2:14][CH2:13]1.ClC1C=C2C(=CC=1)NC=C2C1CCNCC1.ClC[CH2:51][CH2:52][C:53]([N:55]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH2:58][CH2:57][CH2:56]1)=[O:54]>>[ClH:2].[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:5]2[C:4]=1[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:13][CH2:14][N:15]([CH2:51][CH2:52][C:53]([N:55]2[CH2:56][CH2:57][C:58]3[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=3)[CH2:64]2)=[O:54])[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 128313754-(5-chloro-[1H]-indol-3-yl)-piperidineHCID 16638840HCID 16638840, compoundHCID 131724873HCID 131724873, compound

Product 1

HCID 131724872HCID 131724872, compound

Procedure

5-Chloro-3-{1-[4-(3,4-dihydro-2H-quinolin-1-yl)-4-oxobutan-1-yl]piperidin-4-yl}-1H-indole, hydrochloride from 5-chloro-3-(piperidin-4-yl)-1H-indole and 4-chloro-1-(3,4-dihydro-2H-quinolin-1-yl)butan-1-one. Mp 158-162° C. 1H NMR (DMSO-d6): 1.85-1.95 (m, 2H); 1.95-2.20 (m, 6H); 2.60-2.75 (m, 4H); 2.95-3.15 (m, 5H); 3.55 (d, 2H); 3.70 (t, 2H); 7.05-7.25 (m, 6H); 7.40 (d, 1H); 7.75 (s, 1H); 10.45 (broad s, 1H); 11.15 (s, 1H). MS m/z: 436 (MH+), 303.

Sources & evidence

ORD record
ord-cd60348979d04e4b860c0c296f491b3b
Source dataset
uspto-grants-2005_05
Patent number
US06890916B2

Reaction notes

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