tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylate

HRID 2206589Notes

Reaction equation

HRID 2206589 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>>[NH2:8][C:6]1[N:7]=[C:2]([N:12]2[CH2:13][CH2:14][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:11]2)[CH:3]=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 50986448Tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylateYield 28%

Conditions

Temperature
140 °C

Procedure

A mixture of 6-chloropyridin-2-amine (10 g, 78 mmol) and tert-butyl piperazine-1-carboxylate (29 g, 156 mmol) was refluxed at 140° C. for 3 days. The reaction mixture was purified by silica gel column chromatography (elute: petroleum ether/ethyl acetate=2:1) to give tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylate (6 g, 28%). LCMS (M+H) m/z: calcd 278.17. found 279.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (elute: petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-89447d4b2bfa459f91651848991c6e8a
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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