Water → N-(2,6-diisopropylphenyl)-2-[(1-phenylamino-cyclohexylmethyl)amino]acetamide

HRID 1894859Notes

Reaction equation

HRID 1894859 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].N[C:19]1([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1C.O.[CH3:34][N:35](C)C=O>>[CH:15]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[C:6]=1[NH:5][C:3](=[O:4])[CH2:2][NH:35][CH2:34][C:19]1([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:17])[CH3:16]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamideHCID 68630087(1-Amino-methylcyclohexyl)phenylamine

Product 1

HCID 25227156N-(2,6-diisopropylphenyl)-2-[(1-phenylamino-cyclohexylmethyl)amino]acetamideYield 71%

Conditions

Temperature
100 °C

Procedure

340 mg (1.34 mmol) of 2-chloro-N-(2,6-diisopropylphenyl)acetamide (obtained in Example 3/c) are added to 270 mg (1.32 mmol) of (1-amino-methylcyclohexyl)phenylamine (obtained in Example 2/b) in 10 ml of dimethylformamide. The reaction medium is stirred at 100° C. under microwave irradiation for 30 min. It is then poured into water and extracted with ethyl acetate. The organic phases are collected and washed with water and then dried over sodium sulfate. The solvents are evaporated. The residue is chromatographed on silica gel (heptane/ethyl acetate 80/20, v/v). 396 mg of N-(2,6-diisopropylphenyl)-2-[(1-phenylaminocyclohexylmethyl)-amino]acetamide are obtained in the form of a white solid. M.p. 104-6° C., yield=71%.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phases are collected
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvents are evaporated
  6. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20

Sources & evidence

ORD record
ord-a98c3384440c460fb1311e685c759ecf
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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