Sodium Dithionite → 4-(2-Amino-3-benzylamino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 730555Notes

Reaction equation

HRID 730555 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]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]=2[N+:28]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[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]([NH:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:15]=2[NH2:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 578349694-(3-Benzylamino-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 578349834-(2-Amino-3-benzylamino-phenyl)-piperazine-1-carboxylic acid tert-butyl esterYield 92.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-(3-benzylamino-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.200 g, 0.485 mmol) in 5 mL ethanol was added to a solution sodium dithionite (0.565 g, 3.245 mmol) in 10 mL water, and the reaction mixture was heated to 100° C. The mixture was stirred for 5 minutes, cooled to room temperature, and concentrated in vacuo to remove ethanol. A yellow solid precipitates and was filtered and dried under vacuum for 18 hours to give 0.173 g (0.45 mmol, 90%) of 4-(2-amino-3-benzylamino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. MS: 383 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove ethanol
  4. customA yellow solid precipitates
  5. filtrationwas filtered
  6. customdried under vacuum for 18 hours

Sources & evidence

ORD record
ord-6b1a56f2301c4146818d5a22ba69d511
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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