Triethylamine → Tert-butyl 4-(2-(3-nitropyridin-2-yl)ethylamino)piperidine-1-carboxylate

HRID 2378964Notes

Reaction equation

[N+:1]([C:4]1[C:5]([CH:10]=[CH2:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)C>[N+:1]([C:4]1[C:5]([CH2:10][CH2:11][NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To an oven dried 10 mL of a vial, was added 3-nitro-2-vinylpyridine (0.300 g, 2 mmol), 4-amino-1-Boc-piperidine (0.601 g, 3.00 mmol), and ethanol (5 ml). Triethylamine (0.843 ml, 6.00 mmol) was added and the vial was capped and heated at 90° C. for 24 hours. Solvents were removed from the mixture by roto-vap. Silica gel chromatography eluting 2M ammonia in methanol-dichloromethane afforded the title compound in 74% yield. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 8.73 (dd, J=4.58, 1.53 Hz, 1 H) 8.19 (dd, J=8.24, 1.22 Hz, 1 H) 7.33 (dd, J=8.24, 4.58 Hz, 1 H) 3.95 (bs, 2 H) 3.30 (t, J=6.87 Hz, 2 H) 3.10 (t, J=6.71 Hz, 2 H) 2.78 (t, J=11.60 Hz, 2 H) 2.56-2.69 (m, 1 H) 1.76-1.84 (m, 2 H) 1.42 (s, 9 H) 1.13-1.27 (m, 2 H).

Workup

customTo an oven dried 10 mL of a vial,
customthe vial was capped
customSolvents were removed from the mixture by roto-vap
washSilica gel chromatography eluting 2M ammonia in methanol-dichloromethane

Sources & evidence

ORD record: ord-8d80166acf234aeea6fd43764fbbd4f6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470680B2

Reaction notes

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