Morpholine → 4-(4-Bromopyridin-2-yl)morpholine

HRID 594066Notes

Reaction equation

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

Participants

Reactant 3

HCID 8083Morpholine

HCID 8471Triethylamine

HCID 27628514-Bromo-2-fluoropyridine

Product 1

HCID 510639184-(4-Bromopyridin-2-yl)morpholine

Conditions

Temperature: 100 °C

Procedure

To a solution of triethylamine (1.0 equiv.) and 2-fluoro-4-bromopyridine (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 66 hr. LCMS analysis indicated the formation of the desired product (m/z=244.9, Rt=0.36 min). The reaction mixture was concentrated in vacuo to yield 4-(4-bromopyridin-2-yl)morpholine as a light brown solid, (>100%, TEA impurity). LCMS (m/z) (M+H)=244.9, Rt=0.36 min. 1H NMR (400 MHz, <dmso>) δ ppm 3.39-3.55 (m, 4H) 3.59-3.75 (m, 4H) 6.87 (dd, J=5.28, 1.37 Hz, 1H) 7.05 (d, J=1.17 Hz, 1H) 8.00 (d, J=5.48 Hz, 1H).

Sources & evidence

ORD record: ord-75638d31cc584d7c8afdc95947b65e93
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Reaction notes

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