Water → 4-[1-(2-ethoxyethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester

HRID 1840964Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4].[CH2:23]([O:25][CH2:26][CH2:27]Cl)[CH3:24].O>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:24][CH2:23][O:25][CH2:26][CH3:27])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4]

Participants

Conditions

Temperature: 22.5 °C

Procedure

0.75 g of a60% suspension of sodium hydride in mineral oil were suspended in 20 mL of dry DMF and 4 g of 4-(1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester were added to the mixture. 1.91 g of 2-chloroethyl ethyl ether were added dropwise at room temperature and the mixture was stirred for 16 hours at 20-25° C. Water was carefully added and ethyl acetate was used as solvent extractor. The organic layer was separated and washed with water. The solvent was removed under reduced pressure affording 4.58 g of a colorless oil. The product was then crystallised from methyl-t-butyl ether/hexane giving a off white solid.

Workup

customThe organic layer was separated
washwashed with water
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-e128761c65b64770824120e6969773f3
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683096B2

Reaction notes

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