Water → HCID 66794017, compound

HRID 2035302Notes

Reaction equation

[OH:1][C:2]1([C:10]#[N:11])[CH2:7][CH2:6][N:5]([O:8][CH3:9])[CH2:4][CH2:3]1.CN(C)C1C=CN=CC=1.CN(C1C=CN=CC=1)C.[CH3:30][C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:32]=1[CH2:39][C:40](Cl)=[O:41].O>ClCCl>[C:10]([C:2]1([O:1][C:40](=[O:41])[CH2:39][C:32]2[C:31]([CH3:30])=[CH:36][C:35]([CH3:37])=[CH:34][C:33]=2[CH3:38])[CH2:3][CH2:4][N:5]([O:8][CH3:9])[CH2:6][CH2:7]1)#[N:11]

Participants

Conditions

Temperature: -20 °C

Procedure

To a cooled (−20° C.) solution of 4-hydroxy-1-methoxy-piperidine-4-carbonitrile (0.32 g, 2.05 mmol) in 2 ml dichloromethane was added 4-dimethylaminopyridine DMAP (13 mg, 0.05 mmol) under argon. Then (2,4,6-trimethyl-phenyl)-acetyl chloride (0.52 g, 2.64 mmol) dissolved in dichloromethane (3 ml) was added dropwise. The reaction mixture was stirred at −20° C. for 30 minutes, then 30 minutes at 0° C. and finally left stirring overnight at room temperature. The reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel to give pure (2,4,6-trimethyl-phenyl)-acetic acid 4-cyano-1-methoxy-piperidin-4-yl ester (compound P3.5) as white solid, mp 75-78° C. Yield: 480 mg.

Workup

additionwas added dropwise
wait30 minutes at 0° C. and finally left
stirringstirring overnight at room temperature
extractionextracted three times with dichloromethane
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-708333bd89df4ad086d06ccc844eae4b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08574607B2

Reaction notes

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