Orotic Acid → (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt hydrate

HRID 1464929Notes

Reaction equation

HRID 1464929 reaction equation
C(O)(=O)C1NC(=O)NC(=[O:5])C=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]([CH3:23])[C:17]=2[CH:24]=1.[C:25]([OH:35])(=[O:34])[C:26]1[NH:33][C:31](=[O:32])[NH:30][C:28](=[O:29])[CH:27]=1.ClC1C=CC2CCNC[C@H](C)C=2C=1>C(#N)C.C(O)(C)C.O.O.C(O)(=O)C1NC(=O)NC(=O)C=1.ClC1C=CC2CCNC[C@H](C)C=2C=1>[OH2:5].[C:25]([OH:35])(=[O:34])[C:26]1[NH:33][C:31](=[O:32])[NH:30][C:28](=[O:29])[CH:27]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]([CH3:23])[C:17]=2[CH:24]=1

Participants

7

Reactant 3

HCID 967Orotic Acid2×HCID 11658860LorcaserinHCID 56925119(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt

Product 1

HCID 131732654(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt hydrate

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolvent2×HCID 6342AcetonitrileSolventHCID 131732655water. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt hydrateSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt hydrate was prepared by addition of one equivalent of orotic acid to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in acetonitrile or isopropanol at 60° C. Orotic acid, at 60° C., was added drop-wise, in the corresponding solvent, with vigorous stirring. Precipitation occurred immediately and the suspension was allowed to cool and stir overnight. Compound 1 orotate salt hydrate prepared in isopropanol consisted of a mixture of the anhydrous and hydrated forms which was converted to the hydrated form by slurring in isopropanol for two days. Alternatively, (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt hydrate was prepared by slurrying anhydrous (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt in water. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt hydrate had an extrapolated melt/recrystallization onset temperature by DSC of 173° C.

Workup

  1. customPrecipitation
  2. temperatureto cool
  3. customCompound 1 orotate salt hydrate prepared in isopropanol
  4. additionconsisted of a mixture of the anhydrous and hydrated forms which
  5. customby DSC of 173° C.

Sources & evidence

ORD record
ord-bdc49f63db7943f5949758c687ffa54b
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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