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(2-(trifluoromethyl)phenyl)acetic acid → 5,7-Dichloro-1'-(2-(2-(trifluoromethyl)phenyl)acetyl)spiro[isoindoline-1,4'-piperidin]-3-one

HRID 390176
Notes
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Reaction equation

HRID 390176 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[Cl:15][C:16]1[CH:17]=[C:18]2[C:27](=[C:28]([Cl:30])[CH:29]=1)[C:21]1([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[NH:20][C:19]2=[O:31]>>[Cl:15][C:16]1[CH:17]=[C:18]2[C:27](=[C:28]([Cl:30])[CH:29]=1)[C:21]1([CH2:26][CH2:25][N:24]([C:10](=[O:12])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:1])([F:14])[F:13])[CH2:23][CH2:22]1)[NH:20][C:19]2=[O:31]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 594597(2-(trifluoromethyl)phenyl)acetic acidHCID 582957645,7-Dichlorospiro[isoindoline-1,4'-piperidin]-3-one

Product 1

HCID 582957375,7-Dichloro-1'-(2-(2-(trifluoromethyl)phenyl)acetyl)spiro[isoindoline-1,4'-piperidin]-3-one

Procedure

The title compound was prepared following a procedure analogous to that described in Example 31 using 2-(2-(trifluoromethyl)phenyl)acetic acid and 5,7-dichlorospiro[isoindoline-1,4′-piperidin]-3-one. LC-MS Method 3 tR=1.246, min, m/z=457; 1H NMR (CDCl3) 1.43 (d, 2H), 2.62 (m, 1H), 2.78 (m, 1H), 2.90 (t, 1H), 3.40 (t, 1H), 3.88-4.11 (m, 3H), 4.93 (d, 1H), 7.43 (m, 2H), 7.54 (m, 2H), 7.70 (d, 1H), 7.77 (s, 1H), 8.74 (s, 1H)

Sources & evidence

ORD record
ord-0b557531cd9042e0a3f8814525ec7417
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383629B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes