2-((4-Chlorophenoxy)methyl)oxirane → 1-[3-(4-Chlorophenoxy)-2-hydroxypropyl]-4-(3-fluoro-2-pyridyl]piperazine

HRID 2290238

Reaction equation

[F:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:14][C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]2[O:23][CH2:22]2)=[CH:17][CH:16]=1>C(O)(C)C>[Cl:14][C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]([OH:23])[CH2:22][N:11]2[CH2:10][CH2:9][N:8]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:13][CH2:12]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 1-(3-fluoro-2-pyridyl)piperazine (453 mg, 2.5 mmol) in 5 ml of isopropanol stirred under nitrogen at 70° C. was added 4-chlorophenoxy-2,3-epoxypropane (476 mg, 2.5 mmol) portionwise and the solution stirred at 70° C. for 3 hours The solution was concentrated in vacuo and the residual oil chromatographed on silica gel eluting with 5% methanol-chloroform to yield 740 mg (81%) of 1-[3-(4-chlorophenoxy)-2-hydroxypropyl]-4-(3-fluoro-2-pyridyl]piperazine; m.p. 73°-76° C. Analysis satisfactory for C18H21ClFN3O2.

Workup

concentrationwas concentrated in vacuo
customthe residual oil chromatographed on silica gel eluting with 5% methanol-chloroform

Sources & evidence

ORD record: ord-fa35163cc57f44ae8a425d1bdca09f5d
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04616017

Linked notes

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