HCID 58824142, compound → HCID 58824132, compound

HRID 459784Notes

Reaction equation

HRID 459784 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[C:15]=2[C:23]#[N:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[C:15]=2[C:23]#[N:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 58824142HCID 58824142, compound

Product 1

HCID 58824132HCID 58824132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Cyano-3-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (12.172 g, 36.6 mmol) from step 1 was dissolved in ethanol (300 ml) in a Parr flask. The flask was flushed with N2, and Pd/C (1.3 g) was added. The solution was treated with H2 on a Parr apparatus at 30 psi overnight. The mixture was filtered through celite, then washed with EtOAc. After concentration, the residue was purified by flash chromatography to give 4-(3-amino-2-cyano-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. (7.585 g, 69%) MS: (M+H)+303.2.

Workup

  1. customThe flask was flushed with N2, and Pd/C (1.3 g)
  2. additionwas added
  3. additionThe solution was treated with H2 on a Parr apparatus at 30 psi overnight
  4. filtrationThe mixture was filtered through celite
  5. washwashed with EtOAc
  6. concentrationAfter concentration
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c3ec3b0df57e4e7297d7a628370d025d
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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