Triethylamine → N-Cyclohexyl-1-[(2-nitrophenyl)sulfonyl]piperidine-3-carboxamide

HRID 656318Notes

Reaction equation

HRID 656318 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH:14]1([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(#N)C>[CH:14]1([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][N:25]([S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH2:24]2)=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 18071645HCID 18071645, compound

Product 1

HCID 11675603N-Cyclohexyl-1-[(2-nitrophenyl)sulfonyl]piperidine-3-carboxamideYield 60.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-nitrobenzene-1-sulfonyl chloride (12.3 mg) and N-cyclohexylpiperidine-3-carboxamide (TFA salt, 18 mg) from Step 2 in 0.2 mL acetonitrile was added triethylamine (19.3 μL). The reaction mixture was stirred at RT for 2 hours and directly purified by HPLC to give 13.2 mg of desired product. LCMS: m/z 396.1 (M+H)+; 813.3 (2M+Na)+.

Workup

  1. customdirectly purified by HPLC

Sources & evidence

ORD record
ord-f49a806fe3024f128cb4c161d4e9d832
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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