Hydrazine hydrate (1:1) → HCID 21093519, compound

HRID 1350398Notes

Reaction equation

HRID 1350398 reaction equation
O.NN.C([N:7]1[CH2:12][C:11](=[O:13])[NH:10][CH:9]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[C:8]1=[O:28])(=O)C>CN(C=O)C.O>[O:21]([C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][CH:9]1[NH:10][C:11](=[O:13])[CH2:12][NH:7][C:8]1=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21093451HCID 21093451, compound

Product 1

HCID 21093519HCID 21093519, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add hydrazine hydrate (0.7 mL, 14.2 mmol) to a solution of 1-acetyl-3-(3-phenoxy-benzyl)-piperazine-2,5-dione (4.8 g, 14.2 mmol) in DMF (10 mL). Stir 2 h, dilute with water (50 mL) and stir an additional 30 minutes. Filter, wash with water, then cold methanol to obtain the title compound as a white powder (2.8 g, 67%): 1H NMR (CDCl3) δ 2.84 (dd, 1H), 2.96 (d, 1H), 3.05 (dd, 1H), 3.42 (d, 1H), 4.03 (m, 1H), 6.83–6.97 (m, 5H), 7.09 (t, 1H), 7.27 (t, 1H), 7.34 (t, 2H), 7.92 (bs, 1H), 8.12 (s, 1H).

Workup

  1. stirringstir an additional 30 minutes
  2. filtrationFilter
  3. washwash with water

Sources & evidence

ORD record
ord-e4122dad06a04754925a2318d35b1449
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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