HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → Dichloromethane methanol ammonium hydroxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Ethyl oxoacetate | HCID 70211 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | N-(1,3-benzodioxol-5-ylmethyl)-N-methyl-1,3-propanediamine | HCID 22488891 | — |
| Product | Dichloromethane methanol ammonium hydroxide | HCID 21896990 | — |
| Product | 2-[[3-[(1,3-Benzodioxol-5-ylmethyl)amino]propyl]amino]acetic acid ethyl ester | HCID 69742407 | — |
Reaction Steps
To N-(1,3-benzodioxol-5-ylmethyl)-N-methyl-1,3-propanediamine (33 g, 0.15 mol) in CH2Cl2 (500 mL) was added ethyl glyoxalate (30 mL of a 50% toluene solution, 0.15 mol) and sodium triacetoxyborohydride (40 g, 0.19 mol). After stirring for 4 hours, the reaction was washed with aqueous potassium carbonate and the solvent removed in vacuo. Chromatography on silica with CH2Cl2/MeOH/ammonium hydroxide gave 14 g of 2-([3-[(1,3-benzodioxol-5-ylmethyl)amino]propyl]amino]acetic acid, ethyl ester, a compound of formula (Y10).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06864263B2 |
| Source dataset | uspto-grants-2005_03 |
| ORD ID | ord-0ca3bcc1eab0486fb8f8506f5fb0bc4c |
| Source note | uspto-grants-2005_03 |