Pyridine → HCID 68632088, compound

HRID 1894857Notes

Reaction equation

HRID 1894857 reaction equation
[S:1](N)(N)(=[O:3])=[O:2].[NH2:6][CH2:7][C:8]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N1C=CC=C[CH:22]=1>>[NH2:6][CH2:7][C:8]1([N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:1]([CH3:22])(=[O:3])=[O:2])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 82267SulfamideHCID 16227755N-[1-(Aminomethyl)cyclohexyl]aniline

Product 1

HCID 68632088HCID 68632088, compoundYield 50%

Procedure

105 mg (1.09 mmol) of sulfamide are added to a solution of 200 mg of (1-aminomethylcyclohexyl)phenylamine (obtained in Example 2b) in 5 ml of pyridine. The medium is stirred at room temperature for 24 h and then at reflux for 2 h. At room temperature, the medium is evaporated and taken up with ethyl acetate and washed with water. The organic phases are collected and dried over sodium sulfate. The solvents are evaporated. The residue is chromatographed on silica gel (ethyl acetate/heptane). 130 mg of N-(1-aminomethylcyclohexyl)-N-phenylmethanesulfonamide are obtained in the form of a yellow solid. Yield=50%.

Workup

  1. temperatureat reflux for 2 h
  2. customAt room temperature, the medium is evaporated
  3. washwashed with water
  4. customThe organic phases are collected
  5. dry with materialdried over sodium sulfate
  6. customThe solvents are evaporated
  7. customThe residue is chromatographed on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-f129d005be1341bfbd6f141e1daed259
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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