Sodium Carbonate → 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-phenoxypiperidine

HRID 463310Notes

Reaction equation

HRID 463310 reaction equation
Cl.CO.C(O)(=O)C(O)=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([CH2:22][CH2:23][CH2:24][N:25]([CH2:27][C:28]([N:30]3[CH2:35][CH2:34][CH:33]([O:36][C:37]4[CH:42]=[CH:41][CH:40]=[C:39](Cl)[CH:38]=4)[CH2:32][CH2:31]3)=[O:29])[CH3:26])[O:21][CH2:20][CH2:19][O:18]2)=[CH:13][CH:12]=1.[H][H].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([CH2:22][CH2:23][CH2:24][N:25]([CH2:27][C:28]([N:30]3[CH2:31][CH2:32][CH:33]([O:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:34][CH2:35]3)=[O:29])[CH3:26])[O:18][CH2:19][CH2:20][O:21]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 202831291-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalateHCID 21893726Hydrochloride methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 202831171-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-phenoxypiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension prepared from 2.25 g of 5% palladium on carbon, 400 ml of methanol, 0.2 ml of saturated HCl/methanol and 11.19 g (19.3 mmol) of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate was shaken under 50 psi hydrogen at 50° for 4 hours. The mixture was allowed to cool to room temperature and filtered, and the solvent was evaporated to provide an oil. The oil was shaken with saturated sodium carbonate, extracted with ether, dried over potassium carbonate, filtered, and the solvent evaporated to provide 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-phenoxypiperidine.

Workup

  1. filtrationfiltered
  2. customthe solvent was evaporated
  3. customto provide an oil
  4. extractionextracted with ether
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-51b17dd9911a4565b4e424e5ac0c3315
Source dataset
uspto-grants-1985_05
Patent number
US04518713

Reaction notes

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