HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-N-(3-methoxybenzyl)amine dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3-Methoxybenzaldehyde | HCID 11569 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethylamine trifluoroacetate | HCID 22322453 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-N-(3-methoxybenzyl)amine dihydrochloride | HCID 22322447 | — |
Reaction Steps
A suspension of the product of Example 1 step (iv) (0.11 g) in a mixture of DMF (1.5 ml) and 1,2-dichloroethane (3 ml) was stirred under an atmosphere of nitrogen. Sodium triacetoxyborohydride (0.097 g), 3-methoxybenzaldehyde (0.041 g) and triethylamine (0.046 g) were added and the mixture stirred for 18 hours at room temperature. Chloroform and aqueous NaHCO3 solution were added, the organic phase separated, dried and concentrated to a gum. Purification by chromatography (chloroform:triethylamine:methanol, 89:10:1) gave an oil which was treated with 1.0M ethereal hydrogen chloride solution to give the titled product as a solid (0.067 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06946478B2 |
| Source dataset | uspto-grants-2005_09 |
| ORD ID | ord-bc3d67a909334a4f8b08ac049b2fe29c |
| Source note | uspto-grants-2005_09 |