HCID 22605405, compound → HCID 22605396, compound

HRID 2307223Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(Cl)[CH2:11][N:10]([CH:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:4][CH:3]=1>[Ni].C(O)(C)(C)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:11][N:10]([CH:12]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred suspension of Raney Nickel (2.0 g, wet slurry) in tertiary butanol (10 mL) and toluene (50 mL) was added a solution of 3-(4-fluorophenyl)-3-chloro-1-(diphenylrnethyl)azetidine (16) (1.9 g) in toluene (20 mL). The mixture was heated to 80° C. for 6 hours, cooled and filtered through kieselguhr. The filtrate was concentrated in vacuo and partitioned between diethyl ether (3×30 mL) and aqueous potassium carbonate solution (50 mL). The combined organic extracts were washed (water, brine), dried (Na2SO4), and concentrated in vacuo. Recrystallisation from diisopropyl ether gave 3-(4-fluorophenyl)-1-(diphenylmiethyl)azetidine (17) (1.5 g), m.p. 65-66° C. (diisopropyl ether). Found: C, 83.25; H1 6.35; N, 4.41. C22H20FN requires C, 8325; H, 6.35; N, 4.41%.

Workup

temperaturecooled
filtrationfiltered through kieselguhr
concentrationThe filtrate was concentrated in vacuo
custompartitioned between diethyl ether (3×30 mL) and aqueous potassium carbonate solution (50 mL)
washThe combined organic extracts were washed (water, brine)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customRecrystallisation from diisopropyl ether

Sources & evidence

ORD record: ord-b52aadef01864b54a572859d0e48dabf
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831078B1

Reaction notes

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