Trolox → 6-hydroxy-2,5,7,8-tetramethyl-N-(3-morpholinopropyl)chroman-2-carboxamide

HRID 1755588Notes

Reaction equation

HRID 1755588 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[O:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][NH2:40])[CH2:33][CH2:32]1>C1COCC1>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH:40][CH2:39][CH2:38][CH2:37][N:34]1[CH2:35][CH2:36][O:31][CH2:32][CH2:33]1)=[O:16])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 40634TroloxHCID 61055N-(3-Aminopropyl)morpholineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 672629816-hydroxy-2,5,7,8-tetramethyl-N-(3-morpholinopropyl)chroman-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (511 mg, 2.1 mmol) in 10 mL THF was added 356 mg CDI and stirred for 2 h. 3-morpholino-propylamine (438 μl, 432 mg, 3.0 mmol) in 10 mL THF was added dropwise and stirred overnight. The reaction was concentrated, dissolved into 70 mL CH2Cl2, the organics washed once with 50 mL saturated NaCl solution, dried over Na2SO4 and concentrated to brown oil. Flash chromatography yielded 6-hydroxy-2,5,7,8-tetramethyl-N-(3-morpholinopropyl)chroman-2-carboxamide as a pale brown solid.

Workup

  1. stirringstirred overnight
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved into 70 mL CH2Cl2
  4. washthe organics washed once with 50 mL saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to brown oil

Sources & evidence

ORD record
ord-a926af01d0ae4648bb4ac8b851c24bb1
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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