Ethanol → 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide Disulfate

HRID 918893Notes

Reaction equation

HRID 918893 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].C(O)C.[S:21](=[O:25])(=[O:24])([OH:23])[OH:22]>C(O)(C)C>[S:21]([O:23][S:21]([OH:24])(=[O:23])=[O:22])([OH:22])(=[O:25])=[O:24].[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

5

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric Acid2×HCID 119593722-amino-3-methyl-N-[2-(morpholin-4-yl)ethyl]pentanamide

Product 1

HCID 671732042-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide DisulfateYield 212.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide free base (25 g, 0.103 mol) dissolved in absolute, anhydrous ethanol (250 mL, 10 vol) cooled in an ice-water bath was slowly added concentrated sulfuric acid (4 mL, 75 mmol) by dropwise addition. Precipitation immediately occurred causing stirring to stop. The ice-water bath was removed and the addition of ethanol (200 mL) and isopropanol (225 mL) was necessary to restart stirring. The remaining required sulfuric acid (7 mL, 131 mmol) was slowly added in an ethanol:isopropanol solution (2:1, 75 mL). An exotherm (20.8° C.-24.0° C.) was observed. The white slurry was allowed to stir overnight under positive nitrogen pressure. The mixture was then filtered washing with isopropanol (150 mL) and dried under high vacuum (35° C.-40° C.) to afford 33.6 g (75% yield) of 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide Disulfate as a white solid. 1H NMR, LC-MS confirmed the identity and XRD pattern matches the small scale screen sample pattern.

Workup

  1. temperaturecooled in an ice-water bath
  2. additionby dropwise addition
  3. customPrecipitation
  4. customThe ice-water bath was removed
  5. additionthe addition of ethanol (200 mL) and isopropanol (225 mL)
  6. stirringto restart stirring
  7. customAn exotherm (20.8° C.-24.0° C.)
  8. stirringto stir overnight under positive nitrogen pressure
  9. filtrationThe mixture was then filtered
  10. washwashing with isopropanol (150 mL)
  11. customdried under high vacuum (35° C.-40° C.)

Sources & evidence

ORD record
ord-65b77ec3d0534f6295bcdef550ee69cc
Source dataset
uspto-grants-2016_03
Patent number
US09271986B2

Reaction notes

Loading…