Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

HRID 1919056Notes

Reaction equation

HRID 1919056 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14]N(C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].BrC1C=CC([N+]([O-])=[O:31])=NC=1.N1CCOCC1>>[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][O:31][CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8176205-Bromo-2-nitropyridineHCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 29279734-(6-Nitropyridin-3-yl)morpholine

Procedure

Following the procedures as described for 188a and starting with 2 g of 5-bromo-2-nitropyridine and 968 mg morpholine, 255a was obtained as a yellow solid (1 g, 50%). MS: [M+H]+ 210. 1H NMR (500 MHz, CDCl3) δ 8.18 (d, J=9.0, 1H), 8.15 (d, J=3.0, 1H), 7.22 (dd, J=3.0, 1H), 3.90 (t, J=5.0, 4H), 3.42 (t, J=5.0, 4H).

Sources & evidence

ORD record
ord-40bde261fdb1458ca8082045b65c3060
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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