Diethyl Ether → 2-Chloromethyl-3-fluoro-4-morpholinopyridine hydrochloride

HRID 1655229Notes

Reaction equation

HRID 1655229 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:12]([F:13])=[C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:10]=[CH:9][N:8]=1.CCOCC>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:6][C:7]1[C:12]([F:13])=[C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 197911482-Hydroxymethyl-3-fluoro-4-morpholinopyridine

Product 1

HCID 197911192-Chloromethyl-3-fluoro-4-morpholinopyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionyl chloride (1.8 ml) in chloroform (15 ml, alumina dried) was added dropwise to a stirred and cooled solution of 2-hydroxymethyl-3-fluoro-4-morpholinopyridine (1.74 g) in chloroform (20 ml). After 2 hours at room temperature the solution was reduced in volume and ether added. The precipitate was filtered off, washed and dried to give 2-chloromethyl-3-fluoro-4-morpholinopyridine hydrochloride (2.1 g) m.p. 203°-205°.

Workup

  1. additionadded
  2. filtrationThe precipitate was filtered off
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-6ccfa53740ce4b129971d5683eb98513
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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