4-Methylmorpholine → Dextroamphetamine

HRID 500349

Reaction equation

HRID 500349 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.S(O)(O)(=O)=O.[NH2:21][CH:22]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:23].CN1CCOCC1>CN(C=O)C.O1CCOCC1.O>[CH3:23][C@H:22]([NH2:21])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 222898Amphedrine

Product 1

HCID 5826Dextroamphetamine

Reagents, catalysts & solvents 1

HCID 86622776DMF dioxane waterSolvent

Procedure

O-Acetyl-l-carnitine·Cl (1.000 g, 4.17 mmol) was dissolved in 12.5 mL of a mixture of DMF/dioxane/water (2:2:1). NHS (0.528 g, 4.59 mmol) and DCC (0.947 g, 4.59 mmol) were added and the mixture was stirred overnight at ambient temperature. Solvents were evaporated and the remaining residue was dried overnight in high vacuum. The crude succinimidyl ester intermediate was dissolved in 20 mL of anhydrous DMF. Amphetamine sulfate (0.700 g, 1.90 mmol) and NMM (0.92 mL, 8.34 mmol) were added and the mixture stirred overnight. Solvent was evaporated to dryness and the remaining residue was leached with IPA. Solvent was evaporated to yield Carn-d-amphetamine.

Workup

  1. customSolvents were evaporated
  2. customthe remaining residue was dried overnight in high vacuum
  3. dissolutionThe crude succinimidyl ester intermediate was dissolved in 20 mL of anhydrous DMF
  4. stirringthe mixture stirred overnight
  5. customSolvent was evaporated to dryness
  6. customSolvent was evaporated

Sources & evidence

ORD record
ord-684be369b7ea4f9bb6157c8fc9ed90a1
Source dataset
uspto-grants-2010_08
Patent number
US07772222B2

Linked notes

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