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

HRID 867877Notes

Reaction equation

HRID 867877 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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 14306132HCID 14306132, compound

Product 1

HCID 143061332-(Chloromethyl)-4-(piperidin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (3.01 ml) was added dropwise to a stirred solution of 2-hydroxymethyl-4-piperidino-pyrimidine (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.

Workup

  1. temperaturecooled in an ice/salt bath
  2. additionThe solution was poured onto ice
  3. extractionextracted with chloroform
  4. customThe extracts were dried

Sources & evidence

ORD record
ord-2bd5fd9917af4dbbba0adf0b928ca1fe
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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