3-Aminopiperidine-2,6-dione hydrochloride → HCID 16097939, compound

HRID 1915133Notes

Reaction equation

HRID 1915133 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:11]([C:12]([OH:14])=O)[C:10]=1[C:18]([OH:20])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][CH:23]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:24]1=[O:25]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:11]2[C:10]=1[C:18](=[O:20])[N:22]([CH:23]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:24]1=[O:25])[C:12]2=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 20062998HCID 20062998, compound

Product 1

HCID 16097939HCID 16097939, compoundYield 113.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-benzyloxy-phthalic acid (1.08 g, 4.00 mmol) and rac-α-aminoglutarimide hydrochloride (0.65 g, 4.0 mmol) in pyridine (10 mL) was heated to reflux for 4 h. The reaction mixture was cooled and the solvent was evaporated under vacuum. The residue was suspended in ethyl acetate (200 mL) and washed with dilute aqueous HCl (100 mL). The organic phase was combined with the insoluble precipitate and evaporated to dryness. The resulting solid was triturated with ethyl acetate (100 mL), filtered, washed with additional ethyl acetate (50 mL), and dried to give the title compound (1.66 g, 86% yield); mp 238-240° C.: HPLC, Waters Symmetry C-18, 3.9×150 mm, 5 μm, 1 mL/min. 240 nm, 40/60 CH3CN/0.1% H3PO4, 7.23 (96.71%); 1H NMR (DMSO-d6) δ 1.99-2.08 (m, 1H), 2.45-2.62 (m, 2H), 2.81-2.94 (m, 1H), 5.10 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 5.38 (s, 2H), 7.32-7.53 (m, 6H), 7.60 (d, J=8.5 Hz, 1H), 7.83 (t, J=8.2 Hz, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6) δ 22.0, 30.9, 48.8, 70.0, 115.6, 116.6, 120.2, 127.3, 128.0, 128.5, 133.3, 136.2, 137.0, 155.5, 165.3, 166.8, 169.9, 172.8; Anal. Calcd for C20H16N2O5: C, 65.93; H, 4.43; N, 7.69. Found: C, 65.54; H, 4.35; N, 7.63.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated under vacuum
  5. washwashed with dilute aqueous HCl (100 mL)
  6. customevaporated to dryness
  7. customThe resulting solid was triturated with ethyl acetate (100 mL)
  8. filtrationfiltered
  9. washwashed with additional ethyl acetate (50 mL)
  10. customdried

Sources & evidence

ORD record
ord-45f14e477c1e4350b7264f1bbf591500
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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