Hydrochloric Acid → 3,3-dimethyl-2,3-dihydro-1H-inden-1-amine

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Reaction Steps

3,3-Dimethyl-1-(N-methyl-N-methylsulfonyl)aminoindan ##STR18## a) A solution of 25.0 g (0.156 mol) of 3,3-dimethylindan-1-one (Chem. Ber. 64, 1931, 1493) in 700 ml of methanol was stirred with 120.2 g (1.56 mol) of ammonium acetate and 69.1 g (1.1 mol) of sodium cyanoborohydride at 60° C. for 8 h. The reaction mixture was adjusted to pH<2 using dilute hydrochloric acid and concentrated using a rotary evaporator. The residue was taken up in dilute hydrochloric acid and extracted with EA, and the aqueous phase was then made alkaline using potassium carbonate solution and extracted with EA. The organic phase was dried with magnesium sulfate and concentrated under reduced pressure, giving 10.3 g of 1-amino-3,3-dimethylindan.

Provenance & Evidence