2-bromo-3-chlorobenzoic acid → 1-Benzyl-4-piperidone

HRID 2055438Notes

Reaction equation

HRID 2055438 reaction equation
Br[C:2]1[C:10](Cl)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=O.ClC1C2[C:19]3([O:25]C(=O)C=2C=CC=1)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3.CO.Cl>[Pd]>[CH2:4]([N:22]1[CH2:23][CH2:24][C:19](=[O:25])[CH2:20][CH2:21]1)[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

5

Reactant 3

HCID 331232-bromo-3-chlorobenzoic acidHCID 21893726Hydrochloride methanolHCID 69016183HCID 69016183, compound

Product 1

HCID 192201-Benzyl-4-piperidone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the general procedure described in J. Org. Chem. 1976, 41, 2628, from 2-bromo-3-chloro-benzoic acid (the preparation of which is described in J. Org. Chem. 203, 68, 2030) and 1-benzyl-piperidin-4-one was prepared 7-chloro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one, after debenzylation (Pd/C, H2, MeOH/HCl), as a white solid. ES-MS m/e (%): 238.7 (M+H+).

Sources & evidence

ORD record
ord-9f82cc8f794f416aac514abd40fa1ce3
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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