Hydrochloric Acid → Sodium Chloride

HRID 713470Notes

Reaction equation

HRID 713470 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[ClH:26].[OH-].[Na+:28]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[Na+:28].[Cl-:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58270793HCID 58270793, compound

Product 2

HCID 5234Sodium ChlorideHCID 27789574-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate (210 mg, 0.605 mmol) in dioxane (1 mL) was added 4N HCl in dioxane (0.756 mL, 3.0 mmol) and the mixture was stirred for 48 h. 1N NaOH (2.4 mL, 2.4 mmol) was added to neutralize the mixture. The solvent was evaporated, ether was added to the resulting white precipitate and the mixture sonicated. This white precipitate was filtered, washed with ether to give the title compound as a white powder as a NaCl salt (171 mg) and used without further purification. 1H NMR (400 MHz, chloroform-d) δ ppm 8.00-8.16 (m, 2H) 7.24-7.41 (m, 2H) 3.42-3.58 (m, 3H) 3.15-3.29 (m, 3H) 2.31-2.53 (m, 2H) 2.11 (m, 2H); MS (m/z, MH+): 248.3

Workup

  1. customThe solvent was evaporated
  2. additionether was added to the resulting white precipitate
  3. customthe mixture sonicated
  4. filtrationThis white precipitate was filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-785ca3193f674d89a6a4d50f391d32b0
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…