HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 5-Chloro-6-[(1-methylethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 1,1-Dimethylethyl 4-{5-chloro-6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate | HCID 59850180 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Chloro-6-[(1-methylethyl)oxy]-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one | HCID 59850186 | 89.2% |
Reaction Steps
A solution of 1,1-dimethylethyl 4-{5-chloro-6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate (D86, 140 mg, 0.34 mmol) in dichloromethane (3 ml) was treated with trifluoroacetic acid (3 ml) and stirred at room temperature under argon for 1 hr. The mixture was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate (×3). The combined extract was dried (MgSO4) and concentrated under vacuum to leave the title compound as a red oil (94 mg, 83%). M++H=310.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08288412B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-43d69491286847848d4ecfc45730e814 |
| Source note | uspto-grants-2012_10 |