Trifluoroacetic acid → 2-(2-(2-(piperidin-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)isoindoline-1,3-dione

HRID 1096662Notes

Reaction equation

HRID 1096662 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH:23]1[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[CH2:26][CH2:27][CH2:28][CH:23]([C:15]2[N:14]([CH2:13][CH2:12][N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66786754tert-butyl 3-(1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 667869112-(2-(2-(piperidin-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (129A) (4.36 mmoles max, crude mixture) was added to a 20 mL scintillation vial equipped for stirring. CH2Cl2 (3 mL) and trifluoroacetic acid (1 mL) were then added and the resultant solution was allowed to stir at room temperature for 72 hrs. The reaction was concentrated and dried in-vacuo affording 2-(2-(2-(piperidin-3-yl)-1H-benzo[d]imidazol-1-yl)ethyl)isoindoline-1,3-dione (129B) as a mixture that was used without further purification. ESI-MS: m/z 375.3 (M+H)+.

Workup

  1. customvial equipped
  2. stirringto stir at room temperature for 72 hrs
  3. concentrationThe reaction was concentrated
  4. customdried in-vacuo

Sources & evidence

ORD record
ord-8aff025df3af4a6e9cdcf39446f8600e
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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