Sodium Hydroxide → 1-(Propylsulfonyl)-4-(pyridin-2-yl)piperidine-4-carbonitrile
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:13]#[N:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH2:15]([S:18](Cl)(=[O:20])=[O:19])[CH2:16][CH3:17].[OH-].[Na+]>C(Cl)Cl.CCN(C(C)C)C(C)C>[CH2:15]([S:18]([N:10]1[CH2:9][CH2:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)([C:13]#[N:14])[CH2:12][CH2:11]1)(=[O:20])=[O:19])[CH2:16][CH3:17]Participants
Conditions
- Temperature
- 0 °C
Procedure
4-Pyridin-2-ylpiperidine-4-carbonitrile (1-2) (3.55 g, 19 mmole) was dissolved in DCM-DIEA (v/v 5:1, 60 mL) at 0° C. To this solution was added n-PrSO2Cl (2.98, 21 mmole). The reaction mixture was then stirred for 1 h at 0° C. After this time, LCMS indicated that the reaction was completion. 2N NaOH (40 mL) was added and the reaction mixture was stirred 1 h at 0° C. The reaction mixture solution was then extracted with EtOAc (4×200 mL). The combined EtOAc extracts were washed with brine, dried over MgSO4, filtered, concentrated to afford the desired product 1-(propylsulfonyl)-4-pyridin-2-ylpiperidine4-carbonitrile (I-4A) as a yellow-brown solid. Analytical LCMS: single peak (214 nm), 2.642 min. This product was used in next step reaction without further purification.
Workup
- stirringthe reaction mixture was stirred 1 h at 0° C
- extractionThe reaction mixture solution was then extracted with EtOAc (4×200 mL)
- washThe combined EtOAc extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1b58f9f488a240b29a2ed8621758a592
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825135B2
Reaction notes
Loading…