HCID 86621465, compound → HCID 66625025, compound

HRID 416534Notes

Reaction equation

HRID 416534 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][CH2:16][N:17]=[N+]=[N-])(=[O:13])=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>CO>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][CH2:16][NH2:17])(=[O:12])=[O:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 86621465HCID 86621465, compound

Product 1

HCID 66625025HCID 66625025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

250 mg (0.86 mmol) crude 3-azido-propane-1-sulfonic acid (1-isopropyl-piperidin-4-yl)-amide were dissolved in 10 ml MeOH. The solution was evacuated and rinsed with argon several times. 30 mg palladium on charcoal (10%) were added and again the mixture was evacuated and rinsed with argon several times. Finally argon was exchanged by hydrogen (balloon filled with hydrogen) and the mixture was stirred for 4 h at room temperature. The reaction mixture was filtered over “Celite” and the filter residue was washed with 10 ml MeOH. The filtrate was concentrated under vacuo to give crude 3-amino-propane-1-sulfonic acid (1-isopropyl-piperidin-4-yl)-amide as yellow oil. Yield: 200 mg MS (ES+): m/e=264.

Workup

  1. customThe solution was evacuated
  2. washrinsed with argon several times
  3. addition30 mg palladium on charcoal (10%) were added
  4. customagain the mixture was evacuated
  5. washrinsed with argon several times
  6. filtrationThe reaction mixture was filtered over “Celite”
  7. washthe filter residue was washed with 10 ml MeOH
  8. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-3c9295f6805c426dbc5c1d004aba1b22
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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