2-amino-3-methyl-N-[2-(morpholin-4-yl)ethyl]pentanamide → 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide edisylate

HRID 918895Notes

Reaction equation

HRID 918895 reaction equation
[NH2:1][CH:2]([CH:14]([CH3:17])[CH2:15][CH3:16])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:4].O.O.[CH2:20]([S:26]([OH:29])(=[O:28])=[O:27])[CH2:21][S:22]([OH:25])(=[O:24])=[O:23]>CO>[S:22]([CH2:21][CH2:20][S:26]([OH:29])(=[O:28])=[O:27])([OH:25])(=[O:24])=[O:23].[NH2:1][CH:2]([CH:14]([CH3:17])[CH2:15][CH3:16])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:4]

Participants

4

Reactant 2

HCID 119593722-amino-3-methyl-N-[2-(morpholin-4-yl)ethyl]pentanamideHCID 57346009Ethane-1,2-disulfonic acid--water (1/2)

Product 1

HCID 872955632-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide edisylateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide free base (20 g, 0.082 mol) dissolved in methanol (400 mL, 20 vol) was added 1,2-ethanedisulfonic acid dihydrate (18.6 g, 0.082 mol, 1 eq) in one portion. The homogeneous mixture quickly becomes cloudy, and after about 5 min, solids precipitate. Agitation became difficult and an additional 200 mL methanol was added to facilitate stirring. The mixture was stirred at ambient temperature for about 30 min, and then the solids were collected by vacuum filtration. The wet cake was dried in a 40° C. vacuum oven to afford 33.4 g (93% yield) of 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide edisylate as a white solid. 1H NMR confirmed the identity and XRD pattern matches the small scale screen sample pattern.

Workup

  1. customsolids precipitate
  2. additionan additional 200 mL methanol was added
  3. stirringThe mixture was stirred at ambient temperature for about 30 min
  4. filtrationthe solids were collected by vacuum filtration
  5. customThe wet cake was dried in a 40° C. vacuum oven

Sources & evidence

ORD record
ord-b0239c36fd444972ad92bde512d7a116
Source dataset
uspto-grants-2016_03
Patent number
US09271986B2

Reaction notes

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