Piperidine → 4-Piperidin-1-ylindan-1-one O-methyloxime

HRID 451620Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[C:8]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 170 °C

Procedure

4-Bromoindan-1-one O-methyloxime (6.40 g, 26.7 mmol) was added to a mixture of piperidine (2.72 g, 31.9 mmol), sodium tert-butoxide (3.84 g, 40.0 mmol), Pd2(dba)3 (0.74 g, 0.81 mmol) and BINAP (1.49 g, 2.39 mmol) in dioxane (50 mL) under nitrogen atmosphere. The stirred mixture was heated at 170° C. for 5 minutes on the microwave. After cooling to ambient temperature, the reaction mixture was filtered through celite, then silica gel with 25% ethyl acetate in hexane. The filtrate was concentrated to a brown oil and chromatographed on silica gel with 4% ethyl acetate in hexane. Obtained 4-piperidin-1-ylindan-1-one O-methyloxime (4.33 g, 66%) as an orange oil. MS (ESI) m/z: 245.00 [M+H]+. 1H NMR (DMSO-d6) □: 1.55 (m, 2H), 1.64 (m, 4H), 2.79 (m, 2H), 2.91 (m, 6H), 3.87 (s, 3H), 6.94 (dd, 1H), 7.19 (m, 2H).

Workup

temperatureAfter cooling to ambient temperature
filtrationthe reaction mixture was filtered through celite
concentrationThe filtrate was concentrated to a brown oil
customchromatographed on silica gel with 4% ethyl acetate in hexane

Sources & evidence

ORD record: ord-05fa5720cc0f4512930856422aaecc11
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487116B2

Reaction notes

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