Hydrochloric Acid → 1-{2-{N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-ethylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

HRID 463314Notes

Reaction equation

HRID 463314 reaction equation
[ClH:1].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:18]([CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[CH2:25][CH2:24]3)[CH2:19][CH3:20])OCC[O:11]2)=[CH:6][CH:5]=1.Cl.C(=O)(O)[O-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CO>[ClH:36].[ClH:1].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:11])[CH2:15][CH2:16][CH2:17][N:18]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)[CH2:27][CH2:28]2)[CH2:19][CH3:20])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 516892Sodium BicarbonateHCID 20283085HCID 20283085, compound

Product 1

HCID 202831201-{2-{N-[4-(4-Fluorophenyl)-4-oxobutyl]-N-ethylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5.68 g (10.1 mmol) of 1-{2-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-ethylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride, 150 ml of methanol and 70 ml of 3N HCl was heated at reflux for 4 hours under nitrogen and allowed to cool to room temperature. The mixture was neutralized with saturated sodium bicarbonate after which the methanol was evaporated. The residual aqueous solution was made basic with saturated sodium carbonate, extracted twice with ether and dried over potassium carbonate. Evaporation of the solvent provided an oil. The yield of the dihydrochloride was 5.20 g (99%). Recrystallization from ethanol provided 4.16 g (80%) of analytically pure material.

Workup

  1. temperatureat reflux for 4 hours under nitrogen
  2. customwas evaporated
  3. extractionextracted twice with ether
  4. dry with materialdried over potassium carbonate
  5. customEvaporation of the solvent
  6. customprovided an oil
  7. customRecrystallization from ethanol
  8. customprovided 4.16 g (80%) of analytically pure material

Sources & evidence

ORD record
ord-d7caedbd238749b7951d73ccc137b3bc
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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