Diisopropylethylamine → Tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)methylcarbamate

HRID 69831Notes

Reaction equation

HRID 69831 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:12]1.C(N(C(C)C)CC)(C)C>>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:12]1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 2756030tert-butyl N-[(piperidin-3-yl)methyl]carbamate

Product 1

HCID 68184584Tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)methylcarbamateYield 99%

Procedure

The method of Example 1 was followed using 1 eq each of 4-chloro-3-nitropyridine, tert-butyl piperidin-3-ylmethylcarbamate and diisopropylethylamine yielding tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)methylcarbamate (99%). LCMS (m/z): 336.9 (MH+); LC Rt=2.27 min. 1H NMR (CDCl3): δ 8.80 (s, 1H), 8.33 (d, J=6.0 Hz, 1H), 6.85 (d, J=6.3 Hz, 1H), 4.63 (bs, 1H), 3.28-3.46 (m, 2H), 2.89-3.15 (m, 3H), 2.69-2.86 (m, 1H), 1.55-1.99 (m, 5H), 1.45 (s, 9H).

Sources & evidence

ORD record
ord-8a27b18a070044b8ae6fb6ad74f438bc
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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