Sodium Carbonate → HCID 66816521, compound

HRID 1754898Notes

Reaction equation

HRID 1754898 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:10][C:11]1([C:27]#[N:28])[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:26][C:22]1[CH:21]=[C:20]([S:17]([N:14]2[CH2:13][CH2:12][C:11]([NH:10][C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])([C:27]#[N:28])[CH2:16][CH2:15]2)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 75938Cyclohexanecarbonyl chloride2×HCID 66817154HCID 66817154, compound

Product 1

HCID 66816521HCID 66816521, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of cyclohexanecarbonyl chloride (118 μL, 0.880 mmol) in chloroform (0.25 mL) was added to a mixed solution of 4-amino-1-(3-chloro-benzenesulfonyl)-piperidine-4-carbonitrile (120 mg, 0.400 mmol) in chloroform (1.25 mL) and a saturated aqueous sodium carbonate solution (1.25 mL), and the mixture was vigorously stirred at room temperature for 16 hours. Cyclohexanecarbonyl chloride (51 μL) was further added and the mixture was stirred for 2.5 hours. The organic layer and the aqueous layer were then separated, and the aqueous layer was further extracted with chloroform. The organic layers were combined, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was washed with n-hexane to give cyclohexanecarboxylic[1-(3-chloro-benzenesulfonyl)-4-cyano-piperidin-4-yl]-amide as a white solid. This was used in the next step without further purification.

Workup

  1. customThe organic layer and the aqueous layer were then separated
  2. extractionthe aqueous layer was further extracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-58b7354e631e4847b7ac008b0e22ecae
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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