Hydrochloric Acid → HCID 20283087, compound

HRID 463307Notes

Reaction equation

HRID 463307 reaction equation
[ClH:1].[CH2:2]([N:9]([CH2:11][CH2:12][CH2:13][C:14]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[O:18][CH2:17][CH2:16][O:15]1)C)C1C=CC=CC=1.Cl.[H][H]>[Pd].CO>[ClH:1].[CH3:2][NH:9][CH2:11][CH2:12][CH2:13][C:14]1([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[O:15][CH2:16][CH2:17][O:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 20283049HCID 20283049, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20283087HCID 20283087, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of 12 g of 5% palladium on carbon, 135 g (0.369 mol) of 2-[3-(N-benzyl-N-methylamino)propyl]-2-(4-fluorophenyl)-1,3-dioxolane hydrochloride, 0.1 ml of a saturated solution of hydrogen chloride in methanol and 1 liter of methanol was shaken at 40° for 5 hours under 50 psi hydrogen. The suspension was allowed to cool to room temperature, filtered and the solvent evaporated. Trituration with anhydrous ether, followed by filtration provided 94.6 g (0.343 mol, 93%) of 2-(3-[methylamino]propyl)-2-(4-fluorophenyl)-1,3-dioxolane hydrochloride. Crystallization from isopropyl alcohol provided analytically pure material.

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated
  3. filtrationTrituration with anhydrous ether, followed by filtration

Sources & evidence

ORD record
ord-c704451484d84ff3ad5a249045ecbf50
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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