Picolyl chloride hydrochloride → 6-[2-[1-(2-Pyridylmethyl)-4-piperidyl]ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione

HRID 528511Notes

Reaction equation

HRID 528511 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[CH:16]=[C:15]4[O:20][CH2:21][O:22][C:14]4=[CH:13][C:12]=3[C:11]2=[O:23])[CH2:4][CH2:3]1.Cl.Cl[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[CH:16]=[C:15]4[O:20][CH2:21][O:22][C:14]4=[CH:13][C:12]=3[C:11]2=[O:23])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 1180573866-[2-(4-Piperidyl)ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione hydrochloride

Product 1

HCID 729442156-[2-[1-(2-Pyridylmethyl)-4-piperidyl]ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione

Procedure

Compound I-36 was prepared according to the method in example 3, using 6-[2-(4-piperidyl)ethyl]-[1,3]dioxolo[4,5-f]isoindole-5,7-dione hydrochloride (compound II-1) and 2-chloromethylpyridine hydrochloride as the raw materials: 1H NMR (DMSO-d6): δ 1.12-1.19 (m, 3H), 1.48 (q, 2H, J=6.1 Hz), 1.67 (d, 2H, J=9.4 Hz), 1.94 (t, 2H, J=10.3 Hz), 2.76 (d, 2H, J=11.2 Hz), 3.54 (m, 4H), 6.27 (s, 2H), 7.24 (dd, 1H, J=6.8, 5.4 Hz), 7.38 (s, 2H), 7.42 (d, 1H, J=7.8 Hz), 7.74 (td, 1H, J=7.7, 1.4 Hz), 8.64 (d, 1H, J=4.2 Hz): m/z 394 [M+H]+.

Workup

  1. customCompound I-36 was prepared

Sources & evidence

ORD record
ord-b1baede7d9014c4fa16c10c5bef7c2af
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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