HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenethylamine, m-trifluoromethyl- → 2',3'-dihydro-N-[2-[3-(trifluoromethyl)phenyl]ethyl]-spiro[cyclopropane-1,1'-[1H]indene]-5'-methanamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenethylamine, m-trifluoromethyl- | HCID 104223 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | (4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine | HCID 69342889 | — |
| Reactant | 2',3'-Dihydrospiro[cyclopropane-1,1'-indene]-5'-carbaldehyde | HCID 86093835 | — |
| Product | 2',3'-dihydro-N-[2-[3-(trifluoromethyl)phenyl]ethyl]-spiro[cyclopropane-1,1'-[1H]indene]-5'-methanamine | HCID 69513418 | 88% |
Reaction Steps
The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 2′,3′-dihydro-spiro-[cyclopropane-1,1′-[1H]indene]-5′-carboxaldehyde (prepared as described in example S108) (68 mg, 0.40 mmol), 2-(3-trifluoromethylphenyl)-ethylamine (75 mg, 0.40 mmol) and sodium borohydride (22 mg, 0.59 mmol). The desired product (120 mg, 88%) was isolated without further purification as a colorless oil. MS (ISP) 346.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07259183B2 |
| Source dataset | uspto-grants-2007_08 |
| ORD ID | ord-dc85c6bbee3e44b9a7fedf59e2af67f3 |
| Source note | uspto-grants-2007_08 |