Sodium Hydroxide → 1-(4-Bromothiophen-2-yl)-N-methylmethanamine
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Cl.CN.[C:4]([BH3-])#[N:5].[Na+].[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=O)[S:12][CH:13]=1.[OH-].[Na+]>CO>[Br:8][C:9]1[CH:10]=[C:11]([CH2:14][NH:5][CH3:4])[S:12][CH:13]=1Cl.CN.[C:4]([BH3-])#[N:5].[Na+].[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=O)[S:12][CH:13]=1.[OH-].[Na+]>CO>[Br:8][C:9]1[CH:10]=[C:11]([CH2:14][NH:5][CH3:4])[S:12][CH:13]=118 g (260 mmol) of methylamine hydrochloride and then 7.5 g (100 mmol) of sodium cyanoborohydride are successively added to a solution of 10 g (50 mmol) of 4-bromo-2-thiophenecarboxaldehyde in 150 ml of methanol. The reaction medium is stirred at room temperature for 24 hours and then filtered under vacuum. After evaporating the filtrate to dryness, the residue is taken up in dichloromethane. The organic phase obtained is washed with 1N hydrochloric acid solution. The aqueous phase thus obtained is treated with aqueous 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and evaporated under vacuum. 4.5 g (44%) of (4-bromothiophen-2-ylmethyl)methylamine are obtained.
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