HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylpropiolic Acid → 3-Phenylpropynoic acid-[4-(2-diethylaminoethoxy)phenyl]methylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylpropiolic Acid | HCID 69475 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | {4-[2-(Diethylamino)ethoxy]phenyl}methanamine | HCID 235944 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Phenylpropynoic acid-[4-(2-diethylaminoethoxy)phenyl]methylamide | HCID 68816767 | — |
Reaction Steps
A solution of 0.29 g (2 mmol) of phenylpropynoic acid, 0.44 g (2 mmol) of [4-(2-diethylaminoethoxy)phenyl]methylamine, 0.7 g (2.2 mmol) of TBTU, 0.29 g (2.2 mmol) of HOBT and 0.51 mL (3 mmol) of Hünig base in 30 mL of THF and 2 mL of DMF is stirred for 14 hours at ambient temperature. The reaction mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol (80:20)). Yield: 130 mg (18.5% of theory); C22H26N2O2 (M=350.46); calc.: molecular ion peak (M+H)+: 351; found: molecular ion peak (M+H)+: 351; Rf value: 0.39 (silica gel, dichloromethane/methanol (80:20)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07592373B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-d8977cacbe1e46ffbd03041c4a886eb2 |
| Source note | uspto-grants-2009_09 |