Sodium Carbonate → HCID 10707808, compound

HRID 501212Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

1-Benzyl-4-(2-methoxyphenyl)piperidin-4-ol (4.5 g, 15.15 mmol) was mixed with anhydrous potassium bisulphate (8.0 g, 58.56 mmol) and heated to 160° C. under vacuum at 10 mm Hg for 0.5 h. The flask was cooled, the contents dissolved in water and the solution was saturated with sodium carbonate and extracted with ether (2×1100 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure and the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:1) to furnish 1-benzyl-4-(2-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2.0 g, 45%). 1H NMR (200 MHz, CDCl3): δ 2.551-2.573 (m, 2H), 2.67-2.71 (m, 2H), 3.16-3.19 (brs, 2H), 3.66 (s, 2H), 3.79 (s, 3H), 5.76-5.78 (brs, 1H), 6.83-6.92 (m, 2H), 7.15-7.41 (m, 7H); m/e=279 (M+).

Workup

temperatureThe flask was cooled
extractionextracted with ether (2×1100 mL)
washThe organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-78afdc59208b4ee3a1ccc114f9406ad4
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772245B2

Reaction notes

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