2-Bromoanisole → 4-(2-methoxyphenyl)piperidin-4-ol

HRID 1955050Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.C([N:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]1)C1C=CC=CC=1>C1COCC1>[OH:28][C:25]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH2:26][CH2:27][NH:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 15 g of 2-bromoanisole in 50 ml of THF is cooled to -70° C., under nitrogen, a 1.6 M solution of n-butyllithium in THF is added dropwise and the mixture is kept stirring for 1 hour. The mixture is is cooled to -70° C. and a solution of 15.2 g of 1-benzylpiperid-4-one in 50 ml of THF is added dropwise. The mixture is kept stirring while allowing the temperature to rise to RT and after 1 hour, the reaction mixture is concentrated under vacuum. The residue is taken up in AcOEt, the organic phase washed with water, with a saturated solution of NaCl, dried over MgSO4 and the solvent evaporated under vacuum. 14 g of the expected product are obtained after crystallization from the AcOEt/ether/heptane mixture.

Workup

stirringThe mixture is kept stirring
waitto rise to RT and after 1 hour
concentrationthe reaction mixture is concentrated under vacuum
washthe organic phase washed with water, with a saturated solution of NaCl
dry with materialdried over MgSO4
customthe solvent evaporated under vacuum

Sources & evidence

ORD record: ord-40ea86cbebfe43b4ab0021a786be32a9
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124316

Reaction notes

Loading…