Trifluoroacetic acid → (R)-3-(2-chlorobenzamido)-N-methyl-N-(piperidin-4-yl)-2,3-dihydro-1H-indene-5-carboxamide

HRID 1193424Notes

Reaction equation

[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([NH:6][C@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([N:18]([CH:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[CH3:19])=[O:17])[CH:14]=2)[CH2:9][CH2:8]1)=[O:5].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([NH:6][C@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([N:18]([CH3:19])[CH:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)=[O:17])[CH:14]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

(R)-tert-Butyl 4-(3-(2-chlorobenzamido)-N-methyl-2,3-dihydro-1H-indene-5-carboxamido)-piperidine-1-carboxylate (300 mg, 0.587 mmol, 1 eq) was dissolved in dichloromethane (10 ml). The solution was cooled to 0° C., and trifluoroacetic acid (2 ml) was added dropwise. The reaction mixture was stirred for 1 h at room temperature and then concentrated under reduced pressure. The residue was taken up in dichloromethane (100 ml), washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution (in each case 50 ml), dried over sodium sulfate and concentrated under reduced pressure. The desired product was in the form of a brown solid and was used in the next stage without being purified further. Yield: 95% (230 mg, 0.559 mmol)

Workup

concentrationconcentrated under reduced pressure
washwashed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution (in each case 50 ml),
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customwithout being purified further

Sources & evidence

ORD record: ord-52efe166575b40e0aa12caa9d708b965
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680159B2

Reaction notes

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