Potassium Carbonate → HCID 68213446, compound

Participants

Reaction Steps

15 g (74.4 mmol) of methyl 4-(aminomethyl)benzoate hydrochloride, 13.8 g (78.1 mmol) of 8-methoxy-3,4-dihydronaphthalen-2(1H)-one [for the preparation, see WO 2005/012291-A1, Example 45], 14.3 ml (81.8 mmol) of N,N-diisopropylethylamine, 4.7 ml of acetic acid and 20.5 g (96.7 mmol) of sodium triacetoxyborohydride were suspended in 600 ml of dichloromethane and stirred at RT overnight. The reaction mixture was then concentrated and the residue was stirred with ethyl acetate and water at RT for 1 h. The resulting precipitated solid was filtered off with suction. The filtrate phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried and concentrated. The solid obtained above (18.2 g) and the residue of the organic phase (12.9 g) were combined and once more stirred in a mixture of dichloromethane, water and saturated potassium carbonate solution (pH 12) until everything had gone into solution. The organic phase was then separated off, dried and concentrated. The title compound was obtained in the form of the residue.

Provenance & Evidence