Thionyl Chloride → 4-Chloromethyl-5-methyl-6-piperidino pyrimidine hydrochloride

HRID 620167Notes

Reaction equation

HRID 620167 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 143061624-Pyrimidinemethanol,5-methyl-6-(1-piperidinyl)-

Product 1

HCID 212457984-Chloromethyl-5-methyl-6-piperidino pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionyl chloride (4.5 ml) in chloroform (30 ml) was added dropwise to a stirred solution of 4-hydroxymethyl-5-methyl-6-piperidinopyrimidine (4.24 g) in chloroform (30 ml) cooled in an ice-salt bath. The mixture was allowed to warm to room temperature and stirred for a further 22 hours. The solution was stripped to a residual glass which was triturated with diethyl ether to give 4-chloromethyl-5-methyl-6-piperidino-pyrimidine hydrochloride, 5.24 g, m.p. 182°-184°.

Workup

  1. temperaturecooled in an ice-salt bath
  2. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-47cbc3b89caa4caaa7e580236d6fee8b
Source dataset
uspto-grants-1989_04
Patent number
US04820708

Reaction notes

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