Sodium Hydroxide → HCID 39243654, compound

HRID 1169829Notes

Reaction equation

HRID 1169829 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:9]=[C:8]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[CH2:27]([S:30](Cl)(=[O:32])=[O:31])[CH2:28][CH3:29].[OH-].[Na+]>C(Cl)Cl>[CH3:3][C:4]1[N:9]=[C:8]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][N:13]([S:30]([CH2:27][CH2:28][CH3:29])(=[O:32])=[O:31])[CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1.[CH2:27]([S:30]([N:13]1[CH2:12][CH2:11][CH:10]([C:16]#[N:17])[CH2:15][CH2:14]1)(=[O:32])=[O:31])[CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57430045HCID 57430045, compound

Product 2

HCID 39243654HCID 39243654, compoundHCID 59003518HCID 59003518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(6-methylpyridin-2-yl)piperidine-4-carbonitrile dihydrochloride (II-3) (2.74 g, 10 mmole) in DCM (60 mL) containing DIEA (5.16 g, 40 mmole) was added n-C3H7SO2Cl (1.57 g, 11 mmole) at 0° C. The resultant reaction mixture was stirred for 2 h at 0° C. After this time, LCMS indicated that the reaction was completion. 2N NaOH (30 mL) was added to the reaction. The resultant reaction mixture was stirred for 2 h at rt. After this time, the DCM layer was separated. The aqueous solution was extracted with DCM (3×80 mL). The combined DCM solution was washed with brine, dried over MgSO4, filtered and concentrated to afford the desired product 4-6-methylpyridin-2-yl)-1-(propylsulfonyl)piperidine-4-carbonitrile (II-4A). Analytical LCMS: single peak (214 nm), 2.967 min. This product was used in next step reaction without further purification.

Workup

  1. customThe resultant reaction mixture
  2. customThe resultant reaction mixture
  3. stirringwas stirred for 2 h at rt
  4. customAfter this time, the DCM layer was separated
  5. extractionThe aqueous solution was extracted with DCM (3×80 mL)
  6. washThe combined DCM solution was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e8bf2eb9eec7462cac28081a9cb69732
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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