2-(2-Methoxyphenyl)methyl-3-methyl-4-piperidone → 2-(2-Methoxyphenyl)methyl-3-methyl-4-methylene-piperidine

HRID 1281907Notes

Reaction equation

HRID 1281907 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH:16]1[CH:21]([CH3:22])[C:20](=O)[CH2:19][CH2:18][NH:17]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH:16]1[CH:21]([CH3:22])[C:20](=[CH2:1])[CH2:19][CH2:18][NH:17]1

Participants

5

Reactant 2

HCID 110753212-(2-Methoxyphenyl)methyl-3-methyl-4-piperidoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 109988562-(2-Methoxyphenyl)methyl-3-methyl-4-methylene-piperidine

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

20.1 g (56 mmol) of methyl-triphenylphosphonium bromide, 6.3 g (56 mmol) of potassium tert-butoxide and 11 g (47 mmol) of 2-(2-methoxyphenyl)methyl-3-methyl-4-piperidone 15 in 200 mL of abs. THF are used. The product is crystallized from acetone as the oxalate. Yield: 13.1 g (87%); melting point: 145° C.

Workup

  1. customThe product is crystallized from acetone as the oxalate

Sources & evidence

ORD record
ord-6f228702070a4f38ab0f85ccc0710ffb
Source dataset
uspto-grants-2002_09
Patent number
US06455538B1

Reaction notes

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