Sodium Bicarbonate → 4-(4-Bromophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine

HRID 2206230Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 1-benzyl-4-(4-bromophenyl)piperidin-4-ol (3.0 g) in toluene (20 mL) was added p-toluenesulfonic acid monohydrate (1.98 g) at room temperature. The reaction mixture was stirred at 130° C. for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution at 0° C., and the mixture was extracted with ethyl acetate-THF. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (2.80 g).

Workup

extractionthe mixture was extracted with ethyl acetate-THF
washThe organic layer was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-060e86722af94638a1c4c53dd508896f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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