Hydrazine → HCID 57507318, compound

HRID 556478Notes

Reaction equation

HRID 556478 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([N+:12]([O-])=O)[CH:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].NN>C(Cl)Cl.[Ni]>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[NH2:12])(=[O:10])=[O:9])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 206314-Chloro-2-nitrophenylsulfonyl chlorideHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 57507318HCID 57507318, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6344DichloromethaneSolvent

Procedure

The mixture of 4-Chloro-2-nitro-benzenesulfonyl chloride (255 mg, 1 mmol), 4-Amino-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 1 mmol) and K2CO3 (276 mg, 2 mmol) in DCM (3 mL) was stirred at room temperature for 1 hr. The mixture was concentrated in vacuo, the residue was dissolved in methanol, and then Ra—Ni (0.5 g) and hydrazine (1 mL, 17 mmol) was added. The resulting mixture was stirred at room temperature for 2 hr, filtered concentrated in vacuo. The residue was purified by column chromatography to give 380 mg 4-(2-Amino-4-chloro-benzenesulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester as pale white solid. MS: [M+H]+=390

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in methanol
  3. stirringThe resulting mixture was stirred at room temperature for 2 hr
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3955c3b4921946df8137c52c56e75d9c
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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