Hydrochloric Acid → Cinacalcet Hydrochloride

HRID 871110Notes

Reaction equation

HRID 871110 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.[ClH:27]>C1(C)C=CC=CC=1.CCCCCCC>[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:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 156419Cinacalcet2×

Product 1

HCID 156418Cinacalcet HydrochlorideYield 92.55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

Cinacalcet base Compound of formula (I) (5.0 gm) was dissolved in toluene (25 ml) and n-heptane (75 ml), and the pH of the solution was adjusted to 1-2 using concentrated hydrochloric acid at 25-30° C. and stirred for 30 minutes. The precipitated solid was filtered, washed with 10 ml n-heptane, and dried under vacuum to yield 5.1 gm (92.55%) of Cinacalcet hydrochloride; HPLC purity 99.80%; chiral purity: 99.95%.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with 10 ml n-heptane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-792fc4eab3a7433dbc75b753eaab9a78
Source dataset
uspto-grants-2015_03
Patent number
US08969623B2

Reaction notes

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