2-Chloro-5-nitropyridine → Tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate

HRID 2271611Notes

Reaction equation

HRID 2271611 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12]1>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:12]2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 42330413-(Boc-amino)piperidine

Product 1

HCID 66715840Tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamateYield 93.4%

Procedure

Following General procedure H, 2-chloro-5-nitropyridine (500 mg, 3.1 mmol) was reacted with tert-butyl piperidin-3-ylcarbamate (695 mg, 3.5 mmol) followed by reduction to afford the desired product (847 mg, 93%) as a purple solid: ESI MS m/z 293 [C15H24N4O2+H]+.

Sources & evidence

ORD record
ord-11aac89af17647ad9728b4b6934415b9
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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