Process for producing bicycloaniline derivatives

A process for preparing a crystalline form of a 3.5 hydrate of Compound A dihydrochloride, which comprises the steps of:

• (a) concentrating a solution of Compound A in an organic solvent to form a slurry;
• (b) treating the slurry of step (a) with hydrogen chloride in a solvent on heating;
• (c) cooling the slurry of step (b) to room temperature;
• (d) collecting crystals from the resulting slurry of step (c);
• (e) drying the crystals of step (d);
• and
• (f) treating the dried crystals of step (e) with wet inert gas to stabilize water content in the desired crystalline form.

A process for preparing a compound of formula (6):

• or a salt thereof, which comprises the steps of:
• (a) reacting a compound of formula (1):
• with a compound of formula (2):
• X1—CH2CH2—X2 (2)
• wherein X1 and X2 each independently is a leaving group, to obtain a compound of formula (3):
• (b) nitrating a compound of formula (3) to obtain a compound of formula (4):
• (c) reducing oxo groups of the compound of formula (4) to obtain a compound of formula (5):
• or a salt thereof;
• (d) reducing a nitro group of the compound of formula (5) or a salt thereof to obtain a compound of formula (6) or a salt thereof;
• and optionally converting said compound of formula (6) into a salt thereof.