Pyridine → N-(11-(Carbomethoxy)undecanoyl)-N-Methyl-2-Benzyloxyaniline

HRID 1003244Notes

Reaction equation

HRID 1003244 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.[C:23]([O:38][CH3:39])(=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O-:36])=O>C(Cl)Cl>[C:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:36])([O:38][CH3:39])=[O:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 187960752-(Benzyloxy)-N-methylanilineHCID 22672980Dodecanedioic acid, monomethyl ester

Product 1

HCID 18795814N-(11-(Carbomethoxy)undecanoyl)-N-Methyl-2-BenzyloxyanilineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred ice-cold solution of (27) (0.21 g., 1.0 mM) in dried methylene chloride (10 mL) containing anhydrous pyridine (0.3 mL) is added (7) (0.27 g., 1.03 mM), dissolved in 5 methylene chloride (5 mL), dropwise over 1 minute (some methylene chloride used as a rinse). After stirring cold for 30 minutes, the mixture is allowed to stir at ambient temperature for completion of the reaction. The reaction mixture is washed 1× with 1N HCL, dried (Na2SO4) and filtered. Flash chromatography (silica gel, 20% ethyl acetate/hexane as eluant) of the residue obtained gives the title compound (28) (0.33 g) as a colorless oil.

Workup

  1. washa rinse)
  2. stirringto stir at ambient temperature for completion of the reaction
  3. washThe reaction mixture is washed 1× with 1N HCL
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customFlash chromatography (silica gel, 20% ethyl acetate/hexane as eluant) of the residue obtained

Sources & evidence

ORD record
ord-29554f9b9bf44eb3acf21078c2480955
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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