Dimethylamine → Methyl 10-(dimethylamino)-10-oxodecanoate

HRID 2222386Notes

Reaction equation

HRID 2222386 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=[O:13].ON1C2C=CC=CC=2N=N1.[CH:26]1([N:32]=[C:33]=NC2CCCCC2)CCCCC1.CNC>O1CCCC1>[CH3:26][N:32]([CH3:33])[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:15])=[O:13]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 69957Monomethyl sebacateHCID 757711-Hydroxybenzotriazole

Product 1

HCID 12352850Methyl 10-(dimethylamino)-10-oxodecanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the decandioic acid mono methyl ester (2 mmol) in dry tetrahydrofuran (20 ml) was added 1-hydroxybenzotriazole (1 mmol), N,N′-dicyclohexylcarbodiimide (1.1 mmol) and N,N-dimethylamine (2M solution in tetrahydrofuran, 2 ml). The mixture was stirred overnight and then filtered. The solvent was removed in vacuo and the residue redissolved in ethyl acetate. The ethyl acetate solution was washed sequentially with saturated sodium hydrogen carbonate solution, 1M potassium hydrogen sulphate solution and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate and removal of the solvent, the product was purified by preparative layer chromatography on silica plates in ethyl acetate to afford methyl 9-(N,N-dimethylcarbamoyl)nonanoate.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue redissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed sequentially with saturated sodium hydrogen carbonate solution, 1M potassium hydrogen sulphate solution and saturated sodium chloride solution
  5. dry with materialAfter drying over anhydrous magnesium sulphate and removal of the solvent
  6. customthe product was purified by preparative layer chromatography on silica plates in ethyl acetate

Sources & evidence

ORD record
ord-d752238f909941ad833000ea5e67c8c3
Source dataset
uspto-grants-2008_05
Patent number
US07371779B2

Reaction notes

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