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. 2024 Jun 26;25(13):6966. doi: 10.3390/ijms25136966

Table 17.

Mannich-type modifications of (–)–cannabidiol under different conditions.

graphic file with name ijms-25-06966-i032.jpg
conditions 123 (%) 124 (%)
(a) 3.0 equiv. 36% aqueous formaldehyde, 3.0 equiv. NH2nBu, MeOH, room temperature, 7 days 89 –
(b) 3.0 equiv. 36% aqueous formaldehyde, 3.0 equiv. NH2nBu, EtOH, reflux, 20 h 64 21
(c) 3.0 equiv. 36% aqueous formaldehyde, 3.0 equiv. NH2nBu, EtOH, reflux, 6 h then 45 °C, 18 h overnight ~100 0
(d) 3.0 equiv. 36% aqueous formaldehyde, 3.0 equiv. NH2nBu, 1,4-dioxane, reflux, 6 h then 50 °C, 18 h overnight 60 –
(e) 3.0 equiv. 36% aqueous formaldehyde, 3.0 equiv. NEt3, EtOH, reflux, 2 days (reflux, 6 h then 45 °C, 16 h overnight) – 30
(f) 3.0 equiv. 36% aqueous formaldehyde, EtOH, 3 days (reflux, 6 h then 45 °C, 16 h overnight) – 0 a

a bisarylmethane-type side product formed.