Hydrochloric Acid → 2-Chloro-4-fluoro-N-[3-(piperidin-4-yloxy)-phenyl]-benzamide hydrochloride

HRID 1822022Notes

Reaction equation

HRID 1822022 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[Cl:30])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:30].[Cl:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[C:22]([NH:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:16]=1)=[O:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 578936334-[3-(2-Chloro-4-fluoro-benzoylamino)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 690700762-Chloro-4-fluoro-N-[3-(piperidin-4-yloxy)-phenyl]-benzamide hydrochlorideYield 199.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Combine 4-[3-(2-chloro-4-fluoro-benzoylamino)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (preparation 77, 2.99 g, 6.67 mmol), dioxane (30 mL) and a solution of hydrogen chloride in dioxane (4M, 15 mL) and stir at room temperature. After 2 hr., concentrate at reduced pressure to remove the solvent, dry under vacuum to give the title compound as a white solid (2.56 g, 100%): Mass spectrum (ion spray): m/z=349.0 (M+1); Analysis calculated for C18H19Cl2FN2O2.0.25H2O: C, 55.47; H, 5.04; N, 7.19. Found C, 55.26; H, 5.09; N, 6.80.

Workup

  1. concentration, concentrate at reduced pressure
  2. customto remove the solvent
  3. customdry under vacuum

Sources & evidence

ORD record
ord-9047efe7e2b54bc1aa4869748dd95f1f
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

Loading…