Dimethylamine → 5-(Dimethylamino)pentanoic Acid

HRID 713834Notes

Reaction equation

HRID 713834 reaction equation
Br[CH:2]([CH2:6][CH2:7][CH3:8])[C:3]([OH:5])=[O:4].C(=O)(O)[O-].[Na+].[CH3:14][NH:15][CH3:16]>>[CH3:14][N:15]([CH3:16])[CH2:8][CH2:7][CH2:6][CH2:2][C:3]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 11446Pentanoic acid, 2-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 140170205-(Dimethylamino)pentanoic Acid

Procedure

Bromovaleric acid (2 g) was dissolved in aqueous solution of dimethylamine and stirred at room temperature overnight. The solvent was removed on a rotovap and the residue treated with an aqueous solution containing one equivalent of sodium bicarbonate. The solvent was removed, the residue suspended in ethanol and filtered. The solvent was removed from the filtrate and the residue suspended in methylene chloride and suspended again. After filtration, removal of the solvent from the filtrate yielded an oil (1.3 g) that slowly crystallized on storage.

Workup

  1. customThe solvent was removed on a rotovap
  2. additionthe residue treated with an aqueous solution
  3. customThe solvent was removed
  4. filtrationfiltered
  5. customThe solvent was removed from the filtrate
  6. filtrationAfter filtration, removal of the solvent from the filtrate

Sources & evidence

ORD record
ord-386433cabf72491d803a2c2e00360b29
Source dataset
uspto-grants-2015_11
Patent number
US09186325B2

Reaction notes

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