Hydrogen Bromide → HCID 131732658, compound

HRID 1464938Notes

Reaction equation

HRID 1464938 reaction equation
[BrH:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]([CH3:13])[C:7]=2[CH:14]=1.C(OC(C)C)(=[O:17])C>C(#N)C.C(OCC)(=O)C>[OH2:17].[BrH:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]([CH3:13])[C:7]=2[CH:14]=1.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]([CH3:13])[C:7]=2[CH:14]=1.[BrH:1]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 7915Isopropyl AcetateHCID 11658860Lorcaserin

Product 1

HCID 131732658HCID 131732658, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide salt hemihydrate was prepared by the dropwise addition of one equivalent of aqueous HBr (˜48%) to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine free base in isopropyl acetate, acetonitrile, or ethyl acetate with vigorous stirring. The product readily precipitated from the reaction in isopropyl acetate. In acetonitrile the solvent was evaporated to near dryness to obtain a solid. In ethyl acetate, seeds were added and the reaction was allowed to stir unstoppered to initiate crystallization. The reaction was then closed and stirring was continued to afford a yellow suspension. The suspension was filtered and the solid was washed with cold ethyl acetate. The resulting white solid was under nitrogen at ˜38° C., and held overnight at 25° C./75% RH. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide salt hemihydrate had an extrapolated dehydration onset temperature by TGA of about 72.5° C.

Workup

  1. customThe product readily precipitated from the reaction in isopropyl acetate
  2. customIn acetonitrile the solvent was evaporated
  3. customto obtain a solid
  4. customcrystallization
  5. customThe reaction was then closed
  6. stirringstirring
  7. customto afford a yellow suspension
  8. filtrationThe suspension was filtered
  9. washthe solid was washed with cold ethyl acetate
  10. customwas under nitrogen at ˜38° C.
  11. customby TGA of about 72.5° C.

Sources & evidence

ORD record
ord-f9d6954dbd5047d182ed6cd53dc8c513
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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