HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → 6-chloro-2,3,4,9-tetrahydro-2-methyl-9-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-pyrido[3,4-b]indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) | HCID 71600 | — |
| Reactant | 4,4-Diethoxy-N-methylbutan-1-amine | HCID 13994547 | — |
| Reactant | 2-(5-chloro-1-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-indol-3-yl)-N-methylethanamine | HCID 66911626 | — |
| Reactant | 1-(4-Chlorophenyl)-1-(2-(3,3-dimethylcyclopentyl)ethyl)hydrazine | HCID 66911694 | — |
| Reactant | 3-(2-Bromoethyl)-1,1-dimethylcyclopentane | HCID 66911718 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 6-chloro-2,3,4,9-tetrahydro-2-methyl-9-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-pyrido[3,4-b]indole | HCID 44242441 | — |
Reaction Steps
The title compound is prepared by following General Methods 1, 3 and 4 using 4-chlorophenylhydrazine hydrochloride, 3-(2-bromoethyl)-1,1-dimethylcyclopentane, and triethylamine (General Method 1), 1-(4-chlorophenyl)-1-(2-(3,3-dimethylcyclopentyl)ethyl)hydrazine and 4,4-diethoxy-N-methylbutan-1-amine (General Method 3) and 2-(5-chloro-1-(2-(3,3-dimethylcyclopentyl)ethyl)-1H-indol-3-yl)-N-methylethanamine (Example 14), formaldehyde and TFA in acetonitrile (General Method 4).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260429B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-27f24f7570e54901af842e07de19477d |
| Source note | uspto-grants-2016_02 |