Water → Ethyl [(1-phenylaminocyclohexylmethyl)amino]acetate

HRID 1894853Notes

Reaction equation

HRID 1894853 reaction equation
[H-].[Na+].[NH2:3][CH2:4][C:5]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CN(C)C=O>[C:12]1([NH:11][C:5]2([CH2:4][NH:3][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 16227755N-[1-(Aminomethyl)cyclohexyl]aniline

Product 1

HCID 86646976Ethyl [(1-phenylaminocyclohexylmethyl)amino]acetateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

110 mg (2.69 mmol) of sodium hydride are added to a solution of 500 mg (2.45 mmol) of (1-aminomethylcyclohexyl)phenylamine in 20 ml of dimethyl formamide. The solution is stirred for 1 h at room temperature and 270 μl (2.45 mmol) of ethyl bromoacetate are added. The reaction medium is stirred at room temperature for 2 h. It is then poured into water and extracted with ethyl acetate. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated. The residue is chromatographed on silica gel (heptane then heptane/ethyl acetate 90/10, v/v). 530 mg of ethyl [(1-phenylamino-cyclohexylmethyl)amino]acetate are obtained in the form of a colorless oil. Yield=75%.

Workup

  1. stirringThe reaction medium is stirred at room temperature for 2 h
  2. extractionextracted with ethyl acetate
  3. customThe organic phases are collected
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe solvents are evaporated
  7. customThe residue is chromatographed on silica gel (heptane

Sources & evidence

ORD record
ord-61deb9531fe14df592fb3c1901805f1d
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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