Dimethylamine → Ethyl 6-(dimethylamino)hexanoate

HRID 1478966Notes

Reaction equation

HRID 1478966 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-4a6ffd14a9d0445d9bc7a381ac114c71
Source dataset
uspto-grants-2016_08
Patent number
US09404127B2

Reaction notes

Loading…