Diethyl Ether → 2-(Morpholin-4-yl)pyridin-4-amine

HRID 917405Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.CCOCC.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>>[N:14]1([C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][N:5]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 8083Morpholine

HCID 844322-Chloropyridin-4-amine

Product 1

HCID 238188102-(Morpholin-4-yl)pyridin-4-amine

Conditions

Temperature: 200 °C

Procedure

A stirred mixture of 45.8 g (356 mmol) 4-amino-2-chloropyridine in 124 ml morpholine was heated at 200° C. for 30 min in a microwave oven. The resulting yellow solution was then cooled to room temperature whereupon crystals appeared. 400 ml ether was then added and the suspension stirred for 10 minutes before being filtered. The filter cake was washed with ether and dried to afford 92.9 g of crystalline material (87% yield of desired product) which 1H NMR analysis revealed to comprise 60 wt % 2-morpholin-4-yl-pyridin-4-ylamine and 40 wt % morpholine. This material was used in the next step without any further purification. ES-MS m/e (%): 180 (M+H+, 100).

Workup

temperatureThe resulting yellow solution was then cooled to room temperature whereupon crystals
filtrationbefore being filtered
washThe filter cake was washed with ether
customdried

Sources & evidence

ORD record: ord-74d96c9d35db4763ab6a89ae1c9631ac
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273865B2

Reaction notes

Loading…