Triethylamine → 1-Aminopiperidine-2,6-dione

HRID 533365Notes

Reaction equation

HRID 533365 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].CC[N:25](CC)CC>C(Cl)(Cl)Cl>[NH2:25][N:18]1[C:19](=[O:22])[CH2:20][CH2:21][CH2:15][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1345083-Amino-2,6-piperidinedioneHCID 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 μl) in CHCl3 (1 ml) was stirred at room 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-fc361a6e06c64c1fbdbdc621d31d9925
Source dataset
uspto-grants-2014_10
Patent number
US08853253B2

Reaction notes

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