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

HRID 1894860Notes

Reaction equation

HRID 1894860 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 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (3.75 mmol) of sodium hydride are added to a solution of 700 mg (3.42 mmol) of (1-aminomethylcyclohexyl)phenylamine (obtained in Example 2/b) in 20 ml of dimethylformamide. The solution is stirred for 1 h at room temperature and then 310 μl (3.4 mmol) of ethyl bromoacetate are added. The reaction medium is stirred at room temperature for 2 h and 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 80/20, v/v). 652 mg of ethyl [(1-phenylaminocyclohexylmethyl)amino]acetate are obtained in the form of a colorless oil. Yield=65%.

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-55961b0cfd6f44e5b3a57af5427e2f7d
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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