Dimethylamine → Ethyl 6-(dimethylamino)hexanoate

HRID 537826Notes

Reaction equation

HRID 537826 reaction equation
CS([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)=O.[CH3:15][NH:16][CH3:17]>C(O)C>[CH3:15][N:16]([CH3:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 64293806HCID 64293806, compound

Product 1

HCID 13257218Ethyl 6-(dimethylamino)hexanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-(methanesulfonyl)hexanoate was allowed to react in a 5.6M solution of dimethylamine in ethanol (100 mL) for 17 hours. The solution was then concentrated in vacuo to dryness. The resulting bright orange paste was purified by column chromatography (column 5″L×2″W; eluted with a gradient of 100% dichloromethane→1%/0.25%→2%/0.5% MeOH/NH4OH in dichloromethane) to afford the product as a yellow oil.

Workup

  1. concentrationThe solution was then concentrated in vacuo to dryness
  2. customThe resulting bright orange paste was purified by column chromatography (column 5″L×
  3. washeluted with a gradient of 100% dichloromethane→1%/0.25%→2%/0.5% MeOH/NH4OH in dichloromethane)

Sources & evidence

ORD record
ord-8d0206cdf00141ef8a30efbdd0e81347
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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