Hydrochloric Acid → 4-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride

HRID 1487906Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([F:20])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[ClH:21]>O1CCOCC1>[ClH:21].[F:20][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH2:10][NH:11][CH2:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 100-mL round-bottom flask, was placed a solution of tert-butyl 3-(4-cyanophenyl)-3-fluoroazetidine-1-carboxylate (compound 43.3, 1.00 g, 3.62 mmol) in dioxane (10 mL) and HCl in dioxane (4 M in dioxane, 10 mL, 40 mmol). The resulting mixture was stirred for 1 h at 60° C., then cooled and concentrated under reduced pressure. The residue was washed with EtOAc (20 mL) and the product solids were collected by filtration to yield 522 mg (68%) of the title compound as a white solid. m/z (ES+) 177 (M+H)+. 1H NMR (300 MHz, CD3OD): δ 7.91 (d, J=7.8 Hz, 2H), 7.82 (d, J=8.1 Hz, 2H), 4.85-4.52 (m, 4H).

Workup

customInto a 100-mL round-bottom flask, was placed
temperaturecooled
concentrationconcentrated under reduced pressure
washThe residue was washed with EtOAc (20 mL)
filtrationthe product solids were collected by filtration

Sources & evidence

ORD record: ord-c02822f374164290bdbc3fed3b822d43
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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