Water → HCID 22065940, compound

HRID 1828231Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10](Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[CH:17]=[CH:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]1[CH2:9][N:15]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[CH:17]=[CH:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-benzyl-3-chloropiperidine (3.83 g, 18.3 mmol), 1H-pyrrolo[2,3-b]pyridine (4.4 g, 36.5 mmol) and cesium carbonate (17.8 g, 54.8 mmol) in DMSO is stirred at 80° C. under a nitrogen atmosphere for 24 h. The reaction is monitored by thin layer chromatography. Two additional amounts of 1-benzyl-3-chloro-piperidine (3.83 g and 1.91 g) are added at 12 h intervals. After 48 h, the mixture is cooled, treated with water and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine and concentrated in vacuo. The resultant residue is purified by flash chromatography (4–5% methanol in CH2Cl2 as eluent) to afford the title compound as an oil, 6.5 g (60% yield), identified by HNMR and mass spectral analyses.

Workup

waitAfter 48 h
temperaturethe mixture is cooled
extractionextracted with ethyl acetate
washwashed sequentially with water and brine
concentrationconcentrated in vacuo
customThe resultant residue is purified by flash chromatography (4–5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record: ord-5fba69fb800e4437ad57adfbc16c05a6
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07057039B2

Reaction notes

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