Benzocaine → 4-(1-Cyano-cyclohexylamino)benzoic acid ethyl ester

HRID 1966952Notes

Reaction equation

HRID 1966952 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C[Si]([C:24]#[N:25])(C)C>C(O)(=O)C>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:13]2([C:24]#[N:25])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:12][CH:11]=1)[CH3:10]

Participants

5

Reactant 3

HCID 2337Benzocaine2×HCID 7967Cyclohexanone2×HCID 82115Trimethylsilyl cyanide

Product 1

HCID 666186724-(1-Cyano-cyclohexylamino)benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 g (12.1 mmol, 1 eq.) of ethyl 4-aminobenzoate (Starting material 1) are added to a solution of 1.25 g (12.1 mmol, 1 eq.) of cyclohexanone (Starting material 2) in 20 ml of acetic acid at 0° C. The solution is stirred for 15 minutes, and 1.6 ml (12 mmol, 1 eq.) of trimethylsilyl cyanide are added. The reaction medium is stirred for 5 hours at room temperature. It is then poured gently into ice-cold ammonium hydroxide solution and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The residue is precipitated from dichloromethane and heptane. The product 4-(1-cyano-cyclohexylamino)benzoic acid ethyl ester is obtained in the form of a white solid.

Workup

  1. stirringThe reaction medium is stirred for 5 hours at room temperature
  2. additionIt is then poured gently into ice-cold ammonium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe residue is precipitated from dichloromethane and heptane

Sources & evidence

ORD record
ord-51da23ac53b145e1ade427422a139b58
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

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