Acetone → (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine(+/-)-Mandelate Salt Hydrate

HRID 1464931Notes

Reaction equation

HRID 1464931 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[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.O>C(#N)C.C(OCC)(=O)C>[OH2:3].[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[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 4

HCID 180AcetoneHCID 962WaterHCID 1292Mandelic Acid2×HCID 11658860Lorcaserin

Product 1

HCID 131732656(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine(+/-)-Mandelate Salt Hydrate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (±)-mandelate salt hydrate was prepared by the addition of one equivalent of (±)-mandelic acid to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in acetonitrile, ethyl acetate, or acetone at 60° C. (±)-Mandelic acid, at 60° C., was added dropwise, in the corresponding solvent, with vigorous stirring. Addition of water to these three samples precipitated the salt and it was allowed to cool and stir overnight. The resulting solids were recovered by filtration and air-dried in a fume hood overnight. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (±)-mandelate salt hydrate had an extrapolated desolvation onset temperature by DSC of about 74° C.

Workup

  1. additionat 60° C., was added dropwise, in the corresponding solvent, with vigorous stirring
  2. customprecipitated the salt and it
  3. temperatureto cool
  4. filtrationThe resulting solids were recovered by filtration
  5. customair-dried in a fume hood overnight
  6. customby DSC of about 74° C.

Sources & evidence

ORD record
ord-91e3a1e260444382aa5f01800e69bb2a
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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