3,4-Dimethylphenol → HCID 18511661, compound

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Reaction Steps

1,4-Dibromobutane, condensed with 3,4-dimethylphenol according to Ismaïel et al. (J. Med. Chem., 1993, 36, 2519-25), gives 1-[4-bromobutoxy]-3,4-dimethylbenzene with a yield of 86%. The condensation of this compound (according to the same authors) with 1,4-dioxa-8-azaspiro[4.5]decane gives, after deprotection, 1-[4-(3,4-dimethylphenoxy)butyl]-4-piperidone in the form of an orangey oil with a yield of 61%. The reductive amination of this ketone (4.33 g or 15.7 mmol) with methylamine hydrochloride (1.06 g; 15.7 mmol) in the presence of sodium triacetoxyborohydride (4.33 g; 20.5 mmol) according to the protocol of Example 3.1 makes it possible to prepare 5.95 g (Yd: 63%) of the compound of formula 10:

Provenance & Evidence