Sodium Hydroxide → 4-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidine-4-carbonitrile

HRID 2102389Notes

Reaction equation

HRID 2102389 reaction equation
Cl.[N:2]1([C:8]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH2:18]([S:21](Cl)(=[O:23])=[O:22])[CH2:19][CH3:20].[OH-].[Na+]>CCN(C(C)C)C(C)C.C(Cl)Cl>[N:2]1([C:8]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][N:13]([S:21]([CH2:18][CH2:19][CH3:20])(=[O:23])=[O:22])[CH2:12][CH2:11]2)=[O:9])[CH2:3][CH2:4][O:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 662791-Propanesulfonyl chlorideHCID 688129634-(Morpholin-4-ylcarbonyl)piperidine-4-carbonitrile hydrochloride

Product 1

HCID 578030894-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 21638731diisopropylethylamine CH2Cl2Solvent

Procedure

To a solution of 4-(morpholin-4-ylcarbonyl)piperidine-4-carbonitrile hydrochloride (I-3) (10.40 g, 40 mmole) in DIEA-DCM (1:4, 200 mL) was added n-C3H7SO2Cl (6.28 g, 44 mmole) at 0° C. The resultant mixture was stirred for 1 h at 0° C. After this time, LCMS indicated that the reaction was complete. 2N NaOH (60 mL) was added to the reaction. The resultant reaction mixture was stirred for 1 h at rt. After this time, the DCM layer was separated. The aqueous solution was extracted with DCM (3×150 mL). The combined DCM solution was washed with brine, dried over MgSO4, filtered, and concentrated to afford the title compound (I-4) which was pure enough for next step reaction. Analytical LCMS: single peak (214 nm), 2.406 min.

Workup

  1. customThe resultant reaction mixture
  2. customAfter this time, the DCM layer was separated
  3. extractionThe aqueous solution was extracted with DCM (3×150 mL)
  4. washThe combined DCM solution was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33398c38085549acb1b8bed782ebea1f
Source dataset
uspto-grants-2009_08
Patent number
US07576083B2

Reaction notes

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