Ammonium Hydroxide → 4-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetamide

HRID 2417598Notes

Reaction equation

HRID 2417598 reaction equation
[O:1]=[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[C:3]1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]#[N:17])[CH2:11][CH2:10]1.[OH-:18].[NH4+]>S(=O)(=O)(O)O>[O:1]=[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[C:3]1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH2:17])=[O:18])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 155921014-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetonitrile

Product 1

HCID 155921164-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-(2-oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetonitrile (3.0 g; described in Example 3) in conc. sulfuric acid (30 ml) was allowed to stay at room temperature for 3 days. The reaction mixture was poured over ice and conc. ammonium hydroxide slowly while stirring, then extracted with chloroform. Evaporation of the solvent left 2.7 g crude product, which was recrystallized from methanol to yield 2.2 g of the title compound: mp 169°-171° C.; ir(CHCl3) 3500, 3430, 3370, 1685 and 1563 cm-1 ; uv max(MeOH) 351 (ε=9920), 254 (ε=14810) and 221 nm(ε=12090); nmr(CDCl3)δ2.75 (t, 4H), 3.09 (s, 2H), 3.35 (t, 4H), 6.00 (2H) and 6.8 (m, 5H); and Anal. Calcd for C13H17N3O2 : C, 63.14% H, 6.93% N, 16.99% and Found: C, 63.24% H, 7.00% N, 16.99%.

Workup

  1. extractionextracted with chloroform
  2. customEvaporation of the solvent
  3. waitleft 2.7 g crude product, which
  4. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-e7be2c9fd90b473c879351f6b27d292b
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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