Trolox → HCID 21701701, compound

HRID 1596223Notes

Reaction equation

HRID 1596223 reaction equation
Cl.Cl.[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH2:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].[OH:13][C:14]1[C:15]([CH3:30])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH3:29])([C:26](O)=[O:27])[CH2:18][CH2:17]2.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C.C(N(CC)CC)C>[C:3]([N:6]1[CH2:11][CH2:10][N:9]([NH:12][C:26]([C:19]2([CH3:29])[CH2:18][CH2:17][C:16]3[C:21](=[C:22]([CH3:25])[C:23]([CH3:24])=[C:14]([OH:13])[C:15]=3[CH3:30])[O:20]2)=[O:27])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

9

Reactant 4

HCID 40634TroloxHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21701657HCID 21701657, compound

Product 1

HCID 21701701HCID 21701701, compoundYield 32.6%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 1-acetyl-4-aminopiperazine dihydrochloride (300 mg), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (382 mg), 1-hydroxybenzotriazole (244 mg) in N,N-dimethylformamide (6 ml) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodimide hydrochloride (350 mg) and triethylamine (0.78 ml) at 5° C. The mixture was stirred at 5° C. for 2 hours and then poured into ethyl acetate and brine. The organic layer was combined, dried over magnesium sulfate, and concentrated. The residue was crystallized from ethyl acetate to give N-(4-acetyl-1-piperazinyl)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (0.17 g).

Workup

  1. dry with materialdried over magnesium sulfate
  2. concentrationconcentrated
  3. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3b8dbf02919743289a6c6de4da7fb77d
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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