Dimethylamine → (3-Methanesulfonylpropyl)dimethylamine

HRID 2203399Notes

Reaction equation

HRID 2203399 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6].[CH3:9][NH:10][CH3:11]>CCOCC>[CH3:8][S:5]([CH2:4][CH2:3][CH2:2][N:10]([CH3:11])[CH3:9])(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 518920821-Bromo-3-methanesulfonylpropane

Product 1

HCID 86722789(3-Methanesulfonylpropyl)dimethylamineYield 101.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-Bromo-3-methanesulfonylpropane (500 mg, 2.5 mmol) was suspended in a dimethylamine solution (2 M in THF; 10 mL, 20 mmol) and stirred at RT, resulting in a crystalline solid. The reaction was left to stand overnight and the reaction mixture was then diluted with Et2O (10 mL) and filtered. The filtrate was concentrated in vacuo resulting in an orange oily solid which was redissolved in Et2O (10 mL), filtered and concentrated in vacuo to give the title compound as an orange oil (420 mg).

Workup

  1. customresulting in a crystalline solid
  2. waitThe reaction was left
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customresulting in an orange oily solid which
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb7ddbf1c4e14576a3d951e3dfa149c1
Source dataset
uspto-grants-2016_06
Patent number
US09365577B2

Reaction notes

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