Trifluoroacetic acid → HCID 59850173, compound

HRID 2064143Notes

Reaction equation

HRID 2064143 reaction equation
[Br:1][C:2]1[C:24]([CH3:25])=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[C:24]([CH3:25])=[CH:23][C:5]2[N:6]([CH:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59850142HCID 59850142, compound

Product 1

HCID 59850173HCID 59850173, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-(5-bromo-6-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate (D36) (1.32 mmol, 541 mg) was dissolved in dichloromethane (5 mL), trifluoroacetic acid (5 mL) added and the mixture stirred under argon at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure, Na2CO3 (10% aqueous solution) added and the product extracted with ethyl acetate (×3). The organic layers were combined, dried (MgSO4) and the solvent removed under reduced pressure to afford the product as a yellow solid (1.16 mmol, 359 mg, 88%)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, Na2CO3 (10% aqueous solution)
  2. additionadded
  3. extractionthe product extracted with ethyl acetate (×3)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cc9ad6b9d8d34771afd70b1b8b573562
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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