Hydrochloric Acid → 3-Amino-3-methylpiperidine-2,6-dione hydrochloride

HRID 1243547Notes

Reaction equation

HRID 1243547 reaction equation
C(OC([N:11]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]([NH2:19])([CH3:18])[C:12]1=[O:20])=O)C1C=CC=CC=1.[ClH:21].[H][H].O>C(O)C.[Pd]>[ClH:21].[NH2:19][C:13]1([CH3:18])[CH2:14][CH2:15][C:16](=[O:17])[NH:11][C:12]1=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21928242N-Benzyloxycarbonyl-alpha-amino-alpha-methylglutarimideHCID 178418361HCID 178418361, compound

Product 1

HCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochlorideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

N-Benzyloxycarbonyl-α-amino-α-methylglutarimide (2.3 g, 8.3 mmol) was dissolved in ethanol (200 mL) with gentle heat and the resulting solution allowed to cool to room temperature. To this solution was added 4N hydrochloric acid (3 mL) followed by 10% Pd/C (0.4 g). The mixture was hydrogenated in a Parr apparatus under 50 psi of hydrogen for 3 hours. To the mixture was added water (50 mL) to dissolve the product. This mixture was filtered through a Celite pad which was washed with water (50 mL). The filtrate was concentrated in vacuo to afford a solid residue. The solid was slurried in ethanol (20 mL) for 30 min. The slurry was filtered to afford 1.38 g (93%) of α-amino-α-methylglutarimide hydrochloride as a white solid: 1H NMR (DMSO-d6) δ11.25 (s, 1H), 8.92 (s, 3H), 2.84–2.51 (m, 2H), 2.35–2.09 (m, 2H), 1.53 (s, 3H); HPLC, Waters Nova-Pak C18 column, 4 micron, 1 mL/min, 240 nm, 20/80 CH3CN/0.1% H3PO4(aq), 1.03 min (94.6%).

Workup

  1. temperaturewith gentle heat
  2. dissolutionto dissolve the product
  3. filtrationThis mixture was filtered through a Celite pad which
  4. washwas washed with water (50 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a solid residue
  7. filtrationThe slurry was filtered

Sources & evidence

ORD record
ord-b2f5b7a062934630b8ed0d3be0c6cf08
Source dataset
uspto-grants-2006_10
Patent number
US07119106B2

Reaction notes

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