Triethyl phosphite → Diethyl {[5-methyl-2-(piperidin-1-yl)-1,3-thiazol-4-yl]methyl}phosphonate

HRID 2221710Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[S:6][C:7]=1[CH3:8].[P:15]([O:22]CC)([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>C(OCC)(=O)C.CO>[CH3:8][C:7]1[S:6][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:4][C:3]=1[CH2:2][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 1-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl)piperidine (2.7 g) and triethyl phosphite (1.5 g) was stirred at 160° C. for 20 hrs. Excess triethyl phosphite was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (2:1, v/v), then ethyl acetate-methanol (10:1, v/v) to give diethyl {[5-methyl-2-(piperidin-1-yl)-1,3-thiazol-4-yl]methyl}phosphonate as a brown oil (1.4 g, yield 35%). NMR (CDCl3) δ: 1.29 (6H, t, J=7.1 Hz), 1.53-1.74 (6H, m), 2.24 (3H, d, J=4.1 Hz), 3.10 (2H, d, J=20.9 Hz), 3.28-3.46 (4H, m), 4.00-4.21 (4H, m).

Workup

customExcess triethyl phosphite was evaporated under reduced pressure
washeluted with ethyl acetate-hexane (2:1

Sources & evidence

ORD record: ord-a00c2e87e2e64737abceeb9c45d37b98
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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