Potassium Carbonate → Ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate

HRID 1651557Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.00 g (6.61 mmol) of 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 1.43 g (7.90 mmol) of ethyl 3-bromopropionate were dissolved in 10 ml of dioxane, and 1.09 g (7.89 mmol) of potassium carbonate was added to the mixed solution, and then the mixture was stirred under heating at an oil bath temperature of around 80° C. for 8 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using a solvent mixture of chloroform and methanol in the volume ratio 19:1 as are eluent. The desired fraction was concentrated under reduced pressure to give 1.78 g (67%) of ethyl 3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-propionate.

Workup

customAfter the reaction
filtrationthe insolubles were filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was separated by silica gel column chromatography
additiona solvent mixture of chloroform and methanol in the volume ratio 19:1
concentrationThe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record: ord-4ab03042306345c98aef76116f372020
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04929618

Reaction notes

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