3,5-Bis(trifluoromethyl)benzoyl chloride → HCID 53702005, compound

HRID 1738920Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].[N+:18]([C:21]1[CH:37]=[CH:36][C:24]([CH2:25][C@@H:26]2[CH2:31][C@@H:30]([NH:32][C:33](=[O:35])[CH3:34])[CH2:29][CH2:28][NH:27]2)=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:27]1[CH2:28][CH2:29][C@H:30]([NH:32][C:33](=[O:35])[CH3:34])[CH2:31][C@H:26]1[CH2:25][C:24]1[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:37][CH:36]=1)=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

2.49 g (9.0 mmol) of 3,5-bis-trifluoromethylbenzoyl chloride are added in the course of 1 hour at 0-5° C. to a stirred suspension of 2.50 g (9.0 mmol) of (2R*,4S*)-N-[2-(4-nitro-benzyl)-piperidin-4-yl]-acetamide in 20 ml of methylene chloride and 20 ml of a 10% aqueous sodium hydrogen carbonate solution. The mixture is then stirred for 1 hour at 25° C. The organic phase is dried over sodium sulfate, concentrated to dryness by evaporation and chromatographed on silica gel with methylene chloride/methanol. The title compound is obtained in the form of a yellowish resin. TLC: methylene chloride/methanol/conc. ammonia (90:9:0.5) Rf =0.45. 1H-NMR (200 MHz, D2O): rotameric mixture. δ 8.28-7.08 (m, 7H), 5.41 (br d, NH), 5.36-5.20 (m, 0.5H), 4.87-4.73 (m, 0.5H), 4.51-4.30 (m, 1H), 4.00-3.82 (m, 0.5H), 3.60-2.85 (m, 3.5H), 1.98 (s, 3H), 2.30-1.92 (m, 2H), 1.62-1.22 (m, 2H).

Workup

dry with materialThe organic phase is dried over sodium sulfate
concentrationconcentrated to dryness by evaporation
customchromatographed on silica gel with methylene chloride/methanol

Sources & evidence

ORD record: ord-7510dcaa2e2946fe8de5c771da5dfc34
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05965562

Reaction notes

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