15-Crown-5 → Pitolisant

HRID 1376166Notes

Reaction equation

HRID 1376166 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O-:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21]CS([O-])(=O)=O)=[CH:15][CH:14]=1.C1OCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:21][CH2:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3633615-Crown-5HCID 23694275HCID 23694275, compoundHCID 1317262253-(4-Chlorophenyl)propylmesylate

Product 1

HCID 9948102Pitolisant

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium 3-piperidinopropanolate (20 mmol), 7 mmol of 3-(4-chlorophenyl)propylmesylate, and 0.5 mmol of 15-crown-5 in 30 ml of dry toluene were refluxed for 4 hours. The solvent was evaporated and the residue purified by column chromatography on silica gel (eluent: methylene chloride/methanol (90/10)). After removing the solvent under reduced pressure the residue was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography on silica gel (eluent: methylene chloride/methanol (90/10))
  3. customAfter removing the solvent under reduced pressure the residue
  4. customwas crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-0954cbc735564590ba89e9df01d7c926
Source dataset
uspto-grants-2007_01
Patent number
US07169928B2

Reaction notes

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