Dimethylformamide → HCID 70925932, compound

HRID 1910520Notes

Reaction equation

HRID 1910520 reaction equation
C(Cl)(=O)C(Cl)=O.Cl.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1.CN(C=O)C.[C:23]1([C:29](=O)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]/[C:29](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:16])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 99482-PhenylacetophenoneHCID 65578Oxalyl chlorideHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)

Product 1

HCID 70925932HCID 70925932, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl dichloride (236 μl, 2.78 mmol) was added dropwise to a solution of 1-methylpiperidine-4-carboxylic acid hydrochloride (500 mg, 2.78 mmol) in DCM (30 ml) and few drops of DMF (catalytic amount). The reaction was stirred at room temperature for 2 hours. The volatiles were removed under vacuum, and the crude was taken up with pyridine (40 ml). 1,2-Diphenylethanone (546 mg, 2.78 mmol) was added, and the resulting suspension was heated under microwave irradiation at 140° C. for 1 hour. Pyridine was removed under vacuum, and the crude was purified by flash chromatography (DCM/MeOH=95/5) to obtain (E)-1,2-diphenylvinyl 1-methylpiperidine-4-carboxylate (62 mg).

Workup

  1. customThe volatiles were removed under vacuum
  2. temperaturethe resulting suspension was heated under microwave irradiation at 140° C. for 1 hour
  3. customPyridine was removed under vacuum
  4. customthe crude was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-7e83002d1d344583be3e70e060eb2c5f
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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