3-Amino-2,6-piperidinedione → 1-Aminopiperidine-2,6-dione

HRID 1036668Notes

Reaction equation

HRID 1036668 reaction equation
C12(C)C(C)(C)C(CC1)CC2C(Cl)=O.N[CH:15]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:16]1=[O:17].C(OC1C=CC=CC=1C([NH:31]C1CCC(=O)NC1=O)=O)(=O)C>C(Cl)(Cl)Cl>[NH2:31][N:18]1[C:19](=[O:22])[CH2:20][CH2:21][CH2:15][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 1345083-Amino-2,6-piperidinedioneHCID 114831362-Acetoxy-n-(2,6-dioxopiperidin-3-yl)benzamideHCID 534427834,7,7-Trimethyl-3-bicyclo[2.2.1]heptanecarbonyl chloride

Product 1

HCID 199821341-Aminopiperidine-2,6-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of (+)-camphanic chloride (19 mg, 00868 mmol), aminoglutarimide (21 mg, 0.0868 mmol) and Et3N (24) in CHCl3 (1 ml) was stirred at room temperature for 16 hours. The solution was diluted with CHCl3, washed with saturated aqueous solution of NaHCO3, dried over Na2SO4, concentrated and purified by chromatography (silica gel, CH2Cl2; EtOAc=10:1) to give product (16 mg, 60.0% yield) as a colorless gel: 13CNMR (CDCl3) δ 172.6, 169.4, 168.6, 165.5, 90.3, 58.3, 53.3, 48.2, 47.6, 29.2, 28.2, 26.9, 22.7, 14.6, 7.6; MS (CI/CH4) m/z 308 (M+). This compound exhibited angiogenic activity in the assay of Example 13.

Workup

  1. washwashed with saturated aqueous solution of NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by chromatography (silica gel, CH2Cl2; EtOAc=10:1)

Sources & evidence

ORD record
ord-a92f053e10fd4511bcb0f3206f072ba6
Source dataset
uspto-grants-2013_10
Patent number
US08546430B2

Reaction notes

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