Hydrochloric Acid → HCID 69744790, compound

HRID 1815872Notes

Reaction equation

HRID 1815872 reaction equation
[CH3:1][C@H:2]1[C@@H:7]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([F:17])[CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.[ClH:18]>CC(=O)CC>[ClH:18].[CH3:1][C@H:2]1[C@@H:7]([C:8]2[C:16]3[O:15][CH:14]=[CH:13][C:12]=3[CH:11]=[C:10]([F:17])[CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59012639HCID 59012639, compound

Product 1

HCID 69744790HCID 69744790, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 18 gm (71 mMol) racemic cis-3-methyl-4-(5-fluorobenzofur-7-yl)piperidine in 200 mL 2-butanone was treated with 14 gm (71 mMol) of a mixture of (S)-p-methyl- and (S)-p-bromomandelic acids. The recovered salt was collected by filtration. The salt and mother liquors were combined and concentrated under reduced pressure. The residue was dissolved in 750 mL 2-butanone at reflux and then allowed to stand at room temperature for 3 hours. The recovered salt was recrystallized from 325 mL 2-butanone to provide 8 gm of 99% e.e. material. This salt was converted to the corresponding hydrochloride essentially as described in EXAMPLE 31 to provide (−)-cis-3-methyl-4-(5-fluorobenzofur-7-yl)piperidine hydrochloride.

Workup

  1. filtrationThe recovered salt was collected by filtration
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 750 mL 2-butanone
  4. temperatureat reflux
  5. customThe recovered salt was recrystallized from 325 mL 2-butanone
  6. customto provide 8 gm of 99% e.e. material

Sources & evidence

ORD record
ord-fa1fc13dfe0d4fd0bcab61fe9355eb00
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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