6-Chloro-3-piperidin-4-YL-1H-indole → 3-[1-[2-(1-Acetyl-2,3-dihydro-1h-indol-3-yl)ethyl]piperidin-4-yl]-6-chloro-1h-indole

HRID 275716Notes

Reaction equation

HRID 275716 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([CH2:13][CH2:14]S(C)(=O)=O)[CH2:5]1)(=[O:3])[CH3:2].[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:25][NH:26]2)=[CH:22][CH:21]=1>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([CH2:13][CH2:14][N:32]2[CH2:33][CH2:34][CH:29]([C:24]3[C:23]4[C:27](=[CH:28][C:20]([Cl:19])=[CH:21][CH:22]=4)[NH:26][CH:25]=3)[CH2:30][CH2:31]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 120720406-Chloro-3-piperidin-4-YL-1H-indoleHCID 185458861-Acetyl-2,3-dihydro-3-[2-(methanesulphonyl)ethyl]-1H-indole

Product 1

HCID 185459673-[1-[2-(1-Acetyl-2,3-dihydro-1h-indol-3-yl)ethyl]piperidin-4-yl]-6-chloro-1h-indole

Procedure

From 19a and 6-chloro-3-(piperidin-4-yl)-1H-indole (EP Patent publication No 465398-A1). Mp 188-90° C. 1H NMR (DMSO-d6) d 1.70-1.90 (m, 3H), 1.95-2.20 (m, 5H), 2.25 (s, 3H), 2.40 -2.55 (m, 2H), 2.80 (tt, 1H), 3.00-3.10 (m, 2H), 3.40-3.55 (m, 1H), 3.75 (dd, 1H), 4.20 (t, 1H), 6.95 (d, 1H), 7.05 (ddd, 1H), 7.25 (dt, 1H), 7.35 (d, 1H), 7.55 (d, 1H), 8.00 (s, 1H), 8.25 (d, 1H). MS m/z (%): 422 (MH+, 100%), 249 (15%), 146 (19%).

Sources & evidence

ORD record
ord-52376bb8730843baad11c064d725ecb2
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

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