반응 #4474

반응 방정식

water

Paraformaldehyde

dimethylamine hydrochloride

product

6-Bromo-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one

→

solid

수율 67.3%

6-Bromo-3-[(dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one, hydrochloride

수율 67.3%

용매

acetic acid

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 8 h
3. 3
   기타The oil which separated out
4. 4
   기타was triturated with ether (500 ml)

실험 절차

Paraformaldehyde (1.5 g) and dimethylamine hydrochloride (3.75 g) were added to a solution of the product of Stage (iii) (10 g) in acetic acid (70 ml) and then heated to reflux for 8 h. On cooling to ambient temperature the reaction mixture was poured into water (400 ml). The oil which separated out was triturated with ether (500 ml) to give a solid (9 g) which was partitioned between ethyl acetate (2×30 ml) and saturated aqueous sodium carbonate (100 ml). The organic phase was evaporated and the residue purified by flash chromatography (G) to give the pure free base as a solid (0.40 g). A sample (0.4 g) was dissolved in ethanol (10 ml), filtered, and ethereal HCl (6 ml) was added. On addition of dry ether (20 ml), the title compound crystallized as a solid (0.38 g) m.p. 219°-220°.

출처