2-Fluoropyridine → N-t-butoxycarbonyl 2-[1-(pyrid-2-yl)piperidin-4-yl]ethylamine

HRID 350683Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]1CCCCN1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][CH2:18][N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.F[C:27]1[CH:32]=[CH:31]C=C[N:28]=1>CC#N>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]1[CH2:17][CH2:18][N:19]([C:20]2[CH:22]=[CH:31][CH:32]=[CH:27][N:28]=2)[CH2:23][CH2:25]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-t-butoxycarbonyl 2-(piperidin-2-yl) ethylamine (8.1 g) and DIEA (14.1 mL) in CH3CN (29 mL) was added 2-fluoropyridine (3.5 mL) and the resulting mixture was heated in a sealed-tube at 100° C. for three days. Solvent was removed and the crude product was purified via column chromatography (20% EtOAc/hexane) to afford 3.9 g of N-t-butoxycarbonyl 2-[1-(pyrid-2-yl)piperidin-4-yl]ethylamine. 1H NMR (CDCl3) δ=8.16 (dd, J=1.8, 5.0 Hz, 1H), 7.44–7.38 (m, 1H), 6.61 (d, J=8.7 Hz, 1H), 6.53 (dd, J=5.0, 7.2, 1H 4.58 (bs, 1H), 4.23 (d, J=12.6 Hz, 2H), 3.15 (q, J=6.6 Hz, 2H), 2.76 (dt, J=2.7, 12.6 Hz, 2H), 1.75 (d, J=12.6 Hz, 2H), 1.55–1.35 (m, 11H), 1.28–1.15 (m, 3H);

Workup

customSolvent was removed
customthe crude product was purified via column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record: ord-c7e9668c167a4505a6137d75dfe5a067
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183281B2

Reaction notes

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