Sodium Hydroxide → 2-(Chloromethyl)-4-(piperidin-1-yl)pyrimidine

Reaction equation

S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:12]=[C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:10]=[CH:9][N:8]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][C:7]1[N:12]=[C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:10]=[CH:9][N:8]=1

Participants

Procedure

Thionyl chloride (3.01 ml) was added dropwise to a stirred solution of 2-hydroxymethyl-4-piperidinopyrimidine (2.66 g) in chloroform (20 ml) cooled in an ice/salt bath. The mixture was allowed to warm to room temperature and stirred for a further 2.5 hours. The solution was poured onto ice, the pH raised to ca. 8 (NaOH), and extracted with chloroform. The extracts were dried and stripped to give 2-chloromethyl-4-piperidino-pyrimidine (2.92 g) as an unstable oil which was used immediately.