Acetone → HCID 86702387, compound

HRID 1464933Notes

Reaction equation

HRID 1464933 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:24][CH2:23][NH:22][CH2:21][C@H:20]([CH3:25])[C:19]=2[CH:26]=1.CC(C)=O>C(O)(C)C.C(#N)C.C(OCC)(=O)C>[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:24][CH2:23][NH:22][CH2:21][C@H:20]([CH3:25])[C:19]=2[CH:26]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 65041Glucuronic Acid2×HCID 11658860Lorcaserin

Product 1

HCID 86702387HCID 86702387, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt was prepared by addition of a molar equivalent of D-glucuronic acid to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in isopropanol, acetonitrile, ethyl acetate, or acetone at 60° C. D-glucuronic acid, dissolved in the corresponding solvent at 60° C., was added dropwise with vigorous stirring. Precipitation occurred immediately and the suspension was allowed to cool and stir overnight. The resulting solid was recovered by filtration and dried in a fume hood overnight. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt had an extrapolated melting onset temperature by DSC of about 164° C.

Workup

  1. additionwas added dropwise with vigorous stirring
  2. customPrecipitation
  3. temperatureto cool
  4. filtrationThe resulting solid was recovered by filtration
  5. customdried in a fume hood overnight
  6. customby DSC of about 164° C.

Sources & evidence

ORD record
ord-f3cc179d4b6f4a0e84a26f3e520526b6
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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