(2e)-3-(2,6-Dichlorophenyl)acrylic acid → (E)-7-chloro-1'-(3-(2,6-dichlorophenyl)acryloyl)-2-methylspiro[isoindoline-1,4'-piperidin]-3-one

HRID 390161Notes

Reaction equation

HRID 390161 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[N:8]([CH3:16])[C:7]2=[O:17].[Cl:18][C:19]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:20]=1[CH:21]=[CH:22][C:23](O)=[O:24]>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:10][CH2:11][N:12]([C:23](=[O:24])/[CH:22]=[CH:21]/[C:20]3[C:19]([Cl:18])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:30])[CH2:13][CH2:14]1)[N:8]([CH3:16])[C:7]2=[O:17]

Participants

3

Reactant 2

HCID 95321(2e)-3-(2,6-Dichlorophenyl)acrylic acidHCID 582957967-Chloro-2-methylspiro[isoindoline-1,4'-piperidin]-3-one

Product 1

HCID 58295725(E)-7-chloro-1'-(3-(2,6-dichlorophenyl)acryloyl)-2-methylspiro[isoindoline-1,4'-piperidin]-3-one

Procedure

The title compound was prepared following a procedure analogous to that described in Example 1 using 7-chloro-2-methylspiro[isoindoline-1,4′-piperidin]-3-one and 2,6-dichlorocinnamic acid. 1H NMR (CDCl3) 1.82 (m, 2H), 2.99 (m, 2H), 3.35 (s, 3H), 3.68 (m, 1H), 3.88 (m, 1H), 4.18 (m, 1H), 4.49 (m, 1H), 7.06 (d, 1H), 7.1-7.6 (5H), 7.76 (2H).

Sources & evidence

ORD record
ord-fc716c53467943b5a816e05e744c1ac8
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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