1,4-Dioxane hydrochloride → 3-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride

HRID 502460Notes

Reaction equation

HRID 502460 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

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68457795HCID 68457795, compound

Product 1

HCID 684580663-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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+).

Workup

  1. temperaturethe heterogeneous reaction mixture was heated up
  2. temperatureto reflux
  3. customthe solvents were removed by evaporation i.V
  4. customand the residue was dried in high vacuum at rt for 5 hours
  5. customThis crude product was recrystallised from MeCN

Sources & evidence

ORD record
ord-2a23cf50bbe54677817a47a427a17021
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

Loading…