Hydrochloric Acid → Sodium Chloride

HRID 713472Notes

Reaction equation

HRID 713472 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]([CH2:19][C:20]([O:22]C)=[O:21])[CH2:15][CH2:14]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+:25].[ClH:26]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([CH:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:17][CH2:18]3)=[N:10][N:9]=2)=[CH:6][CH:7]=1.[Na+:25].[Cl-:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71227279HCID 71227279, compound

Product 2

HCID 5234Sodium ChlorideHCID 71226800HCID 71226800, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)piperidin-1-yl)acetate (97.8 mg, 0.306 mmol) in ethanol (1 mL) was added 2 N NaOH (1 mL). The cloudy reaction suspension was stirred for 4 h until LCMS confirmed the reaction was complete. The mixture was treated with 0.7 mL 1 N HCl dropwise until pH 7. The solvent was evaporated and the residue triturated with ether. The precipitate was filtered, washed with ether and dried under high vacuum, yielding the title compound as a white solid as a NaCl salt (130 mg) which was used without further purification. 1H NMR (400 MHz, chloroform-d) δ ppm 8.10 (dd, J=9.03, 5.02 Hz, 2H) 7.33 (t, J=8.78 Hz, 2H) 3.47 (br. s., 4H) 3.30 (s, 2H) 3.43-3.55 (br. s., 2H) 2.28-2.45 (m, 2H) 2.07-2.28 (m, 2H). MS (m/z, MH+): 306.3

Workup

  1. customThe cloudy reaction suspension
  2. customThe solvent was evaporated
  3. customthe residue triturated with ether
  4. filtrationThe precipitate was filtered
  5. washwashed with ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-7c28efb20f4244feb596aed06597588e
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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