Sulfuric Acid → HCID 131732657, compound

HRID 1464936Notes

Reaction equation

HRID 1464936 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]([CH3:17])[C:11]=2[CH:18]=1.C(OC(C)C)(=O)C>C(#N)C>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]([CH3:17])[C:11]=2[CH:18]=1.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]([CH3:17])[C:11]=2[CH:18]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7915Isopropyl AcetateHCID 11658860Lorcaserin

Product 1

HCID 131732657HCID 131732657, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemisulfate salt was prepared by the drop-wise addition of 0.5 mole equivalent of concentrated sulfuric acid to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine free base in either isopropyl acetate or acetonitrile with vigorous stirring. Precipitation occurred immediately and the suspension was allowed to stir for 1 to 2 days. The resulting yellow solid was recovered by filtration. Acetone was added to the solid followed by sufficient water to cause dispersal (<5%). This mixture was slurried for 4 h and the solid was collected by centrifuge filtration (10,000 rpm for 1 min). The filtrate contained an oil droplet and the filter cake had a small amount of color at the bottom. The white upper portion of the filter cake was removed and air-dried overnight to leave the title salt as a white solid. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemisulfate salt had an extrapolated melting onset temperature by DSC of about 79° C.

Workup

  1. customPrecipitation
  2. filtrationThe resulting yellow solid was recovered by filtration
  3. additionAcetone was added to the solid
  4. waitThis mixture was slurried for 4 h
  5. filtrationthe solid was collected by centrifuge filtration (10,000 rpm for 1 min)
  6. customThe white upper portion of the filter cake was removed
  7. customair-dried overnight

Sources & evidence

ORD record
ord-becaac1cacd54395892e49bf92be0d0c
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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