HCID 23508428, compound → HCID 23508443, compound

HRID 1883692Notes

Reaction equation

HRID 1883692 reaction equation
C([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:15][CH3:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C>[CH2:15]([N:14]([C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:26][CH:25]=1)[CH3:16]

Participants

4

Reactant 2

HCID 23508428HCID 23508428, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23508443HCID 23508443, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The procedure of Preparation Example 9 was repeated, except that 111 mg of 4-[N-(4-benzyloxybenzyl)-N-ethylamino]benzonitrile was used in place of 4-[N-(4-benzyloxybenzyl)-N-methylsulfonylamino]phenyl methanesulfonate, and 3 ml of ethyl acetate was used in place of dioxane. The resulting mixture was stirred for 4 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered to remove any insoluble matter, and the solvent was distilled off from the filtrate. The resulting crude product was purified by TLC (using a 1:1 mixture of ethyl acetate and hexane as the developing solvent) to obtain 29 mg of 4-[N-ethyl-N-(4-hydroxybenzyl)amino]benzonitrile.

Workup

  1. customThe procedure of Preparation Example 9
  2. filtrationThe reaction mixture was filtered
  3. customto remove any insoluble matter
  4. distillationthe solvent was distilled off from the filtrate
  5. customThe resulting crude product was purified by TLC (
  6. additiona 1:1 mixture of ethyl acetate and hexane as the developing solvent)

Sources & evidence

ORD record
ord-d028f53fdb8249b28371d39f9ff2b841
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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