1-(3-Fluoro-2-pyridinyl)piperazine → 1-[3-(2-Cyanophenoxy)-2-hydroxypropyl]-4-(3-fluoro-2-pyridyl)piperazine

HRID 2290239Notes

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.[C:14]([C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1[O:18][CH2:19][CH:20]1[O:22][CH2:21]1)#[N:15]>C(O)(C)C.CCCCCC>[C:14]([C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1[O:18][CH2:19][CH:20]([OH:22])[CH2:21][N:11]1[CH2:10][CH2:9][N:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:12]1)#[N:15]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-(3-fluoro-2-pyridyl)piperazine (453 mg, 2.5 mmol) in 5 ml of isopropanol stirred at 70° C. under nitrogen was added portionwise 2-cyanophenoxy-2,3-epoxypropane (438 mg, 2.5 mmol) and the mixture stirred for 21/2 hours at 70° C. The solvent was removed in vacuo at room temperature and the residual oil was chromatographed on silica gel eluting with 5% methanol-chloroform. The product was obtained as a colorless oil which slowly solidified upon trituration in hexane to yield 0.66 g of 1-[3-(2-cyanophenoxy)-2-hydroxypropyl]-4-(3-fluoro-2-pyridyl)piperazine; m.p. 68°-70° C. Analysis satisfactory for C19H21FN4O2.

Workup

customThe solvent was removed in vacuo at room temperature
customthe residual oil was chromatographed on silica gel eluting with 5% methanol-chloroform
customThe product was obtained as a colorless oil which

Sources & evidence

ORD record: ord-8f171575cdc84df4a117f7a9212a0927
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04616017

Reaction notes

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