ChemicalBook CAS DataBase List 3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole

3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole synthesis

6synthesis methods

Product Name:3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole
CAS Number:2805-84-7
Molecular formula:C13H12F3N
Molecular Weight:239.24

108-94-1

368-90-1

3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole

2805-84-7

16A. Synthesis of 6-(trifluoromethyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole To a solution of 4-(trifluoromethyl)phenylhydrazine (4.71 g, 26.74 mmol) in ethanol (20 mL) was added concentrated hydrochloric acid (10 drops) followed by a solution of cyclohexanone (2.62 g, 26.74 mmol) in ethanol (4 mL). The reaction mixture was stirred at room temperature for 45 minutes and subsequently concentrated under vacuum. The resulting solid was dissolved in a mixture of acetic acid (21 mL) and concentrated sulfuric acid (3.5 mL). The reaction mixture was heated at 85 °C for 30 min, cooled to room temperature and poured into ice water. The suspension formed was filtered and the solid was dried to give 6-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazole as a brown solid (6.01 g, 94% yield). Mass spectrum (electrospray positive ion mode) m/e 240 [M + H]+.

108-94-1 Synthesis

108-94-1
584 suppliers
$12.00/50g

368-90-1
160 suppliers
$15.00/1g

2805-84-7
37 suppliers
$24.00/250mg

Yield:2805-84-7 94%

Reaction Conditions:

Stage #1: cyclohexanone;4-(trifluoromethyl)phenylhydrazinewith hydrogenchloride in ethanol at 20; for 0.75 h;
Stage #2: with sulfuric acid;acetic acid at 85; for 0.5 h;

Steps:

16.a

16a. 6-(Trifluoromethyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole To (4-trifluoromethyl-phenyl)-hydrazine (4.71 g, 26.74 mmol) in ethanol (20 mL) was added concentrated hydrochloric acid (10 drops) followed by a solution of cyclohexanone (2.62 g, 26.74 mmol) in ethanol (4 mL). The reaction was stirred at ro temperature for 45 minutes and concentrated in vacuo. The resulting solid was dissolved in a mixture of acetic acid (21 mL) and concentrated sulfuric acid (3.5 mL). The reaction was heated at 85° C. for 30 minutes, cooled to room temperature, and poured into ice water. The resulting suspension was filtered and dried to give the title compound as a tan solid (6.01 g, 94%). MS (ES+) m/e 240 [M+H]⁺.

References:

US2009/170882,2009,A1 Location in patent:Page/Page column 14

110-52-1 Synthesis