Morpholine → HCID 59542482, compound

HRID 1809104Notes

Reaction equation

Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10]2)=[O:8])[CH:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.[Cu]I.[Cu]>[CH3:15][C:11]1([CH3:16])[CH2:12][CH2:13][CH2:14][N:9]([C:7]([C:4]2[CH:3]=[C:2]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[S:6][CH:5]=2)=[O:8])[CH2:10]1

Participants

Conditions

Temperature: 70 °C

Procedure

(5-Bromo-thiophen-3-yl)-(3,3-dimethyl-piperidin-1-yl)-Methanone (0.1 g) was dissolved in N,N-dimethylethanol (0.5 mL). Copper (I) iodide (0.003 g), copper powder (0.001 g), morpholine (0.045 mL) and potassium phosphate tribasic (0.001 g) were added. The mixture was heated to 70° C. and stirred overnight then diluted with water (2 mL) and the solvent evaporated. The residue was purified by flash chromatography on silica, eluting with 0-60% ethyl acetate in cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a gum (0.008 g). LCMS m/z 309.15 [M+H]+ RT=9.77 min (Analytical Method 1). 1H NMR δ (ppm)(CHCl3-d): 6.7 (s, 1H), 6.2 (s, 1H), 4.8 (m, 4H), 3.6-3.5 (m, 2H), 3.3 (m, 2H), 3.1 (m, 4H), 1.6 (m, 2H), 1.5 (m, 2H), 0.9 (s, 6H).

Workup

customthe solvent evaporated
customThe residue was purified by flash chromatography on silica
washeluting with 0-60% ethyl acetate in cyclohexane
additionThe fractions containing the desired product
customevaporated

Sources & evidence

ORD record: ord-94c993852d26440b98bb3dc0b0f952ec
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362008B2

Reaction notes

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