Hydrochloric Acid → N-(5-Chloropyridin-2-yl)-2-(4-oxopiperidin-1-ylcarbonyl)aminobenzamide

HRID 988661Notes

Reaction equation

HRID 988661 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]([N:19]2[CH2:28][CH2:27][C:22]3(OCC[O:23]3)[CH2:21][CH2:20]2)=[O:18])=[N:6][CH:7]=1.Cl.CCOC(C)=O>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]([N:19]2[CH2:20][CH2:21][C:22](=[O:23])[CH2:27][CH2:28]2)=[O:18])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21906181HCID 21906181, compound

Product 1

HCID 21906655N-(5-Chloropyridin-2-yl)-2-(4-oxopiperidin-1-ylcarbonyl)aminobenzamideYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzamide (120 mg, 0.289 mmol) in dioxane (1 mL) and water (0.25 mL) was treated with 12 N HCl (0.25 mL). After 1.5 h, the mixture was poured into EtOAc and water. The organic layer was washed with satd sodium bicarbonate (2×), brine, dried with sodium sulfate, and concentrated yielding 100 mg of the title compound; which was used without further purification.

Workup

  1. washThe organic layer was washed with satd sodium bicarbonate (2×), brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-55ffe47eece3463a9b00494c7a4ff0b9
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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