1-Benzyl-4-piperidone → 1'-Benzyl-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

HRID 270051Notes

Reaction equation

HRID 270051 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19](Cl)[CH:20]=[CH:21][C:16]=3[C:15](=[O:23])[O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=CC([F:34])=CC=1C(O)=O.C(N1CCC(=O)CC1)C1C=CC=CC=1.C([Li])CCC>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][C:20]([F:34])=[CH:21][C:16]=3[C:15](=[O:23])[O:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 27781812-Bromo-5-fluorobenzoic acidHCID 122130471'-Benzyl-6-chloro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-oneHCID 178418339Butyllithium

Product 1

HCID 673778971'-Benzyl-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This reaction was performed as described for (i) above using 2-bromo-5-fluorobenzoic acid (2.19 g, 10.0 mmol), 1-benzylpiperidin-4-one (3.78 g, 20.0 mmol), n-butyl lithium (n-BuLi) (20 mL) and THF (20 mL) to give the sub-titled compound.

Sources & evidence

ORD record
ord-6270015648f2484cb820595c68701494
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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