Formaldehyde → 4-Chloro-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzeneethanamine

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The compound of formula (P14), in which n=2 and R″ is chloro, was prepared from 4-chloro-N-[(trimethylsilyl)methyl]benzeneethanamine (5.17 g, 21.38 mmol) (Preparation 11), added dropwise to ice-cooled aqueous formaldehyde (37% w/v, 2.3 g, 28.34 mmol). After 10 min., MeOH (3 mL, 74 mmol) was added and the mixture stirred at 0° C. for 3 h. Anhydrous K2CO3 (1 g) was then added and the mixture stirred for 30 min at 0° C. The layers were separated and the aqueous phase extracted with τ-Bu methyl ether. The combined organic layers were dried over MgSO4 and concentrated to yield the titled compound as a pale yellow oil (6.35 g). 1H NMR (CDCl3): 7.21 (2H, d, J=8.4 Hz), 7.09 (2H, d, J=8.4 Hz), 4.03 (2H, s), 3.21 (3H, s), 2.8-2.9 (2H, m), 2.65-2.8 (2H, m), 2.22 (2H, s), 0.03 (9H, s).

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