Diethyl Ether → (+)-6-Acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

A solution of 0.5 g (1.8 mmol) of (+)-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 75 mL of benzene was treated with 5 mL of 2.0M methylmagnesium bromide in diethyl ether. The reaction mixture was refluxed for 2 days. The reaction mixture was cooled and excess Grignard reagent was decomposed with addition of a saturated NH4Cl solution. The benzene layer was separated and washed once with a saturated NaCl solution. The organic solution was evaporated to an oil. The oil was dissolved in 25 mL of 5N HCl and the solution was stirred at room temperature for 30 min. The acidic solution was made alkaline with the addition of excess concentrated NH4OH solution. The basic mixture was extracted twice with CH2Cl2. The combined organic solution was washed once with a saturated NaCl solution and dried over MgSO4. The CH2Cl2 solution was evaporated to yield 0.5 g off an oil. Chromatography of this oil over silica gel with ethyl acetate as eluent gave 0.4 g (75%) of product an oil which upon standing solidified.

1. temperatureThe reaction mixture was refluxed for 2 days
2. temperatureThe reaction mixture was cooled
3. customThe benzene layer was separated
4. washwashed once with a saturated NaCl solution
5. customThe organic solution was evaporated to an oil
6. dissolutionThe oil was dissolved in 25 mL of 5N HCl
7. additionwith the addition of excess concentrated NH4OH solution
8. extractionThe basic mixture was extracted twice with CH2Cl2
9. washThe combined organic solution was washed once with a saturated NaCl solution
10. dry with materialdried over MgSO4
11. customThe CH2Cl2 solution was evaporated
12. customto yield 0.5 g off an oil

ORD record

ord-8585a401f2de495992d8f69cad51c1a0

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05364856