Acetyl chloride → N-{2-[4-(4-Propoxy-phenylethynyl)-phenyl]-propyl}-acetamide

HRID 76207Notes

Reaction equation

HRID 76207 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:22])[CH2:20][NH2:21])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH:19]([CH3:22])[CH2:20][NH:21][C:23](=[O:25])[CH3:24])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 666107682-[4-(4-Propoxy-phenylethynyl)-phenyl]-propylamine

Product 1

HCID 66610435N-{2-[4-(4-Propoxy-phenylethynyl)-phenyl]-propyl}-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.12 g (0.41 mmol) 2-[4-(4-propoxy-phenylethynyl)-phenyl]-propylamine (I65) in 5.0 mL DCM are consecutively added 0.14 mL (1.02 mmol) TEA and 34.9 μL (0.49 mmol) acetyl chloride. The reaction mixture is stirred at r.t. for 3 h. The solvent is removed in vacuo and the residue is purified by HPLC (MeOH/H2O/NH3).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-b5832b506e704d008fa481d3c01dbbd2
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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