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

HRID 1464928Notes

Reaction equation

HRID 1464928 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=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.CC(C)=O>C(O)(C)C.C(OCC)(=O)C>[C:1]([OH:11])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=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

6

Reactant 3

HCID 180AcetoneHCID 967Orotic Acid2×HCID 11658860Lorcaserin

Product 1

HCID 56925119(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt 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 isopropanol, ethyl acetate, or acetone 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. The resulting solid was recovered by filtration and air-dried in a fume hood overnight. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt had an extrapolated initial melting onset temperature by DSC of 236° C.

Workup

  1. customPrecipitation
  2. temperatureto cool
  3. filtrationThe resulting solid was recovered by filtration
  4. customair-dried in a fume hood overnight
  5. customby DSC of 236° C.

Sources & evidence

ORD record
ord-3472921a5b7c41b6a30dc01077da7322
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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