Dimethylformamide → N-picolyl piperidine sulfonamide
Reaction equation
N1C=CC=CC=1CN1CCC([S:18]([N:21]2[CH2:26][CH2:25][CH:24](OC3C=CC(OC(F)(F)F)=CC=3)[CH2:23][CH2:22]2)(=[O:20])=[O:19])(C(OC)=O)CC1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52]Cl.C[N:55](C)C=O>>[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52][NH:55][S:18]([N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)(=[O:19])=[O:20]Participants
Conditions
- Temperature
- 35 °C
Procedure
Part I: Preparation of methyl 1-(2-pyridinylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. The unsubstituted piperidine sulfonamide from part H (7.9 g, 16.95 mmol) was dissolved in dry dimethylformamide (35 mL) and potassium carbonate (7.05 g, 51.1 mmol) and 2-picolyl chloride hydrochloride (4.21 g, 25.67 mmol) were added. The reaction was stirred at 35° C. for sixteen hr and then concentrated in vacuo. The residue was taken up in ethyl acetate and filtered through Celite. The filtrate washed with water two times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexanes) provided the N-picolyl piperidine sulfonamide as a white solid (6.8 g, 72%).
Workup
- concentrationconcentrated in vacuo
- filtrationfiltered through Celite
- washThe filtrate washed with water two times, saturated sodium chloride solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ce267b546c104d41880163c34c3b0832
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372758B1
Reaction notes
Loading…