N-Methylaniline → HCID 67359938, compound

HRID 1664497Notes

Reaction equation

HRID 1664497 reaction equation
C(Cl)(=O)C(Cl)=O.[O:7]=[C:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1.[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[CH3:17][N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([CH:11]1[CH2:10][CH2:9][C:8](=[O:7])[CH2:13][CH2:12]1)=[O:16]

Participants

8

Reactant 5

HCID 7515N-MethylanilineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 1927304-Oxocyclohexanecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 67359938HCID 67359938, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.89 g, 7.0 mmol) and a few drops of dry DMF are added to a stirred solution of 4-oxo-cyclohexanecarboxylic acid (0.50 g, 3.5 mmol) in CH2Cl2 (7 ml) and the reaction is kept stirring at rt overnight. The volatiles are removed under reduced pressure, the residue is azeotroped with toluene and dried under high vacuum yielding crude acid chloride. This material is reacted without further purification with N-methylaniline (0.16 g, 1.5 mmol) in CH2Cl2 (7 ml) in the presence of DIEA (0.58 g, 4.5 mmol). After stirring overnight at rt, saturated aqueous NaHCO3 is added and the mixture extracted three times with CH2Cl2. The combined organic layers are dried over Na2SO4 and evaporated. The residue is column chromatographed on silica gel (hexane/EtOAc 2:1) and the title compound is obtained as a pale yellow solid (0.47 g) in 57% yield. tR (LC-4) 0.89 min; ESI-MS (positive ion): m/z 231.98 [M]+ (calcd 231.13 for C14H17NO2).

Workup

  1. customThe volatiles are removed under reduced pressure
  2. customthe residue is azeotroped with toluene
  3. customdried under high vacuum
  4. customyielding crude acid chloride
  5. stirringAfter stirring overnight at rt
  6. extractionthe mixture extracted three times with CH2Cl2
  7. dry with materialThe combined organic layers are dried over Na2SO4
  8. customevaporated
  9. customchromatographed on silica gel (hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-e3b71921d43f40a088c7890a82b3b8d1
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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