Piperidine → HCID 43803863, compound

HRID 404692Notes

Reaction equation

HRID 404692 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.O.O=[CH:11][C:12]([OH:14])=[O:13].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C(#N)C>[N:15]1([CH:11]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[C:12]([OH:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 581760Thiophene-3-boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 43803863HCID 43803863, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thiophen-3-ylboronic acid (300 mg, 2.34 mmol) was added to a solution of 2-oxoacetic acid hydrate (216 mg, 2.34 mmol) and piperidine (0.23 ml, 2.34 mmol) in acetonitrile (11.7 ml). The mixture was heated to reflux for 5 hours. The reaction was cooled to room temperature and the suspension was filtered on a buckner funnel washing with acetonitrile (8 ml). The title compound (528 mg, quantitative yield) was collected from the filter as an off-white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationthe suspension was filtered on a buckner funnel
  4. washwashing with acetonitrile (8 ml)

Sources & evidence

ORD record
ord-e244d72b40cc48f899ca6d7e589b49ff
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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