Morpholine → 4-(6-Chloro-4-iodopyridin-2-yl)morpholine

HRID 594076Notes

Reaction equation

C(N(CC)CC)C.Cl[C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[C:11]([Cl:16])[N:10]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[Cl:16][C:11]1[N:10]=[C:9]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:14]=[C:13]([I:15])[CH:12]=1

Participants

Reactant 3

HCID 8083Morpholine

HCID 8471Triethylamine

HCID 117373932,6-Dichloro-4-iodopyridine

Product 1

HCID 584413324-(6-Chloro-4-iodopyridin-2-yl)morpholine

Conditions

Temperature: 100 °C

Procedure

To a solution of triethylamine (1.0 equiv.) and 2,6-dichloro-4-iodopyridine (1.0 equiv.) at RT was added morpholine (1.0 equiv) in one portion, the resulting mixture was then heated in an oil bath at 100° C. for 18 hours. LCMS analysis indicated the formation of the desired product (M+H=324.9/326.8, Rt=0.98 min). Water was then added, and the mixture was extracted with ethyl acetate, and the combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was chromatographed via ISCO to yield 4-(6-chloro-4-iodopyridin-2-yl)morpholine as a light brown solid (63%). LCMS (m/z) (M+H)=324.9/326.8, Rt=0.98 min.

Sources & evidence

ORD record: ord-f9dab2e3391a49e9a78ece55dc2402c0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Reaction notes

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