1,4-Dioxane hydrochloride → 3-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:29])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][C:26](=[O:28])[NH2:27])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:30].O1CCOCC1>CCO>[ClH:30].[C:26]([CH2:25][O:24][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([O:22][CH3:23])[CH:19]=1)[C:15]([NH:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:29])(=[O:28])[NH2:27]Participants
4
Procedure
2.20 g (5.4 mmol) of 4-(3-carbamoylmethoxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester was suspended under argon in 40 mL of EtOH at rt; while stirring, 6.75 mL of HCl/dioxane (4 molar) was added; the heterogeneous reaction mixture was heated up to reflux to achieve a clear solution. After cooling down to rt, the solvents were removed by evaporation i.V. and the residue was dried in high vacuum at rt for 5 hours. This crude product was recrystallised from MeCN to yield 1.53 g of 3-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride as colorless solid [MS: 308.3 (MH+)]; the mother liquor contained 0.80 g of [3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-acetic acid ethyl ester hydrochloride as light yellow amorphous solid. MS: 337.3 (MH+).