Cinacalcet → Cinacalcet Hydrochloride

HRID 2038587Notes

Reaction equation

HRID 2038587 reaction equation
[CH3:1][C@@H:2]([NH:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12.CC(O)C.[ClH:31]>C(OCC)(=O)C>[CH3:1][C@@H:2]([NH:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12.[ClH:31]

Participants

4

Reactant 2

HCID 156419CinacalcetHCID 21912024Isopropanol hydrochloride

Product 1

HCID 156418Cinacalcet HydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

Cinacalcet (0.25 moles, 91 gms) was taken in a reaction vessel and IPA/HCl (85 ml) was added dropwise and stirred for about 15 minutes. The solvent was distilled at 50-55° C. under high vacuum to obtain a residue. The residue was suspended in ethyl acetate (516 ml) and heated to reflux temperature until a clear solution was obtained and the solution stirred for about 30 minutes. The solution was cooled to 0-5° C. and stirred to obtain a solid. The solid was washed with ethyl acetate (2×85 ml) and dried at 55-60° C. to obtain the title compound (70 gms, Yield 70%, HPLC purity=98.5%).

Workup

  1. distillationThe solvent was distilled at 50-55° C. under high vacuum
  2. customto obtain a residue
  3. temperatureheated
  4. temperatureto reflux temperature until a clear solution
  5. customwas obtained
  6. stirringthe solution stirred for about 30 minutes
  7. stirringstirred
  8. customto obtain a solid
  9. washThe solid was washed with ethyl acetate (2×85 ml)
  10. customdried at 55-60° C.

Sources & evidence

ORD record
ord-d75ae66d666d475ab3d1f85050436c70
Source dataset
uspto-grants-2013_11
Patent number
US08575393B2

Reaction notes

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