Triethylamine → Levetiracetam

HRID 2197659Notes

Reaction equation

HRID 2197659 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][NH:7][CH:8]([C:11](=[O:13])[NH2:12])[CH2:9][CH3:10].C(N(CC)CC)C.OC1C=CC=CN=1>O1CCCC1.C1(C)C=CC=CC=1>[CH3:10][CH2:9][C@H:8]([N:7]1[C:3](=[O:2])[CH2:4][CH2:5][CH2:6]1)[C:11]([NH2:12])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9877677Methyl-4-(1-carbamoylpropylamino)butyrateHCID 178516071HCID 178516071, compound

Product 1

HCID 5284583Levetiracetam

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Hydrochloride salt of methyl-4-(1-carbamoylpropylamino)butyrate (VId) (0.7 g, 2.9 mmol) is dissolved in a mixture of tetrahydrofuran (10 ml) and triethylamine (0.6 g, 2 equiv.). The suspension is filtered and filtrates are concentrated to dryness to afford an oil. The resulting residue is dissolved in toluene (15 ml) and 2-hydroxypyridine (53 mg, 0.56 mmol, 20 mol %) is added. The mixture is heated to 80° C. until complete conversion. After 3 days (GC: 100% conversion) the mixture is concentrated to dryness under reduced pressure.

Workup

  1. filtrationThe suspension is filtered
  2. concentrationfiltrates are concentrated to dryness
  3. customto afford an oil
  4. concentrationAfter 3 days (GC: 100% conversion) the mixture is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b8a1de58066b4f37819224912b810818
Source dataset
uspto-grants-2012_12
Patent number
US08338621B2

Reaction notes

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