Cinnamic Acid → (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine trans-cinnamate salt

HRID 1464930Notes

Reaction equation

HRID 1464930 reaction equation
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=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(#N)C>[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=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

4

Reactant 2

HCID 444539Cinnamic AcidHCID 11658860Lorcaserin

Product 1

HCID 56925140(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine trans-cinnamate salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine trans-cinnamate salt was prepared by combining one equivalent of trans-cinnamic acid with (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in acetonitrile at 50° C. The sample was cooled slowly and stirred overnight. The resulting white solid was isolated by filtration and dried. Similar samples prepared in isopropanol, acetone or THF produced white solids only after removal of solvent and trituration with MTBE. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine trans-cinnamate salt had an extrapolated melting onset temperature by DSC of 106° C.

Workup

  1. customat 50° C
  2. temperatureThe sample was cooled slowly
  3. customThe resulting white solid was isolated by filtration
  4. customdried
  5. customSimilar samples prepared in isopropanol
  6. customacetone or THF produced white solids only after removal of solvent and trituration with MTBE
  7. customby DSC of 106° C.

Sources & evidence

ORD record
ord-ab93591aca7e4ddfbcd87ff0ad28080b
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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