Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetamide | HCID 178 | — |
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Aniline | HCID 6115 | — |
| Reactant | 2,3-Dimethylaniline | HCID 6893 | — |
| Reactant | 2',3'-Acetoxylidide | HCID 8656 | — |
| Reactant | 2,3-Dimethyl-6-nitroaniline | HCID 597166 | — |
| Reactant | 2,3-Dimethyl-6-nitrophenyl isothiocyanate | HCID 18316482 | — |
| Reactant | 1-(Chloromethyl)cyclopentan-1-amine hydrochloride | HCID 69992485 | — |
| Product | 1-Aminocyclopentanemethanol | HCID 66307 | — |
| Product | HCID 178426721 | HCID 178426721 | — |
Reaction Steps
2,3-Dimethylaniline was protected as 2,3-dimethylacetanilide according to Method A2a, step 1. The acetamide was converted to 2,3-dimethyl-6-nitroaniline, then deprotected according to Method A2a, step 2. The aniline was converted to 2,-dimethyl-6-nitrophenyl isothiocyanate according to Method A2a, step 3. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 2,3-dimethyl-6-nitrophenyl isothiocyanate according to Method C1e to give 2-(2,3-dimethyl-6-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(2,3-dimethyl-6-nitrophenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06353006B1 |
|---|
| Source dataset | uspto-grants-2002_03 |
|---|
| ORD ID | ord-4668162cb9304d0c8dedc64c9b463a9c |
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| Source note | uspto-grants-2002_03 |
|---|
