L-Glutamic Acid → HCID 56929575, compound

HRID 1464932Notes

Reaction equation

HRID 1464932 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]([CH3:22])[C:16]=2[CH:23]=1>CCO.O.C(OC(C)C)(=O)C.O>[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]([CH3:22])[C:16]=2[CH:23]=1

Participants

6

Reactant 2

HCID 33032L-Glutamic Acid2×HCID 11658860Lorcaserin2×

Product 1

HCID 56929575HCID 56929575, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7915Isopropyl AcetateSolvent2×HCID 19096565Water ethanolSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-glutamate salt was prepared by addition of L-glutamic acid (0.5-1 eq.) in hot EtOH/H2O (˜2:1) to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in isopropyl acetate, followed by evaporation of the solvent overnight to produce a solid. The solid was slurried in isopropyl acetate and then isolated by filtration. Alternatively, (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-glutamate salt was prepared by addition of a solution of L-glutamic acid (1 eq.) in hot H2O to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine. The product crystallized without the need for evaporation of the solvent. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-glutamate salt had an extrapolated melting onset temperature by DSC of about 187° C.

Workup

  1. customfollowed by evaporation of the solvent overnight
  2. customto produce a solid
  3. customisolated by filtration
  4. customThe product crystallized without the need for evaporation of the solvent
  5. customby DSC of about 187° C.

Sources & evidence

ORD record
ord-1cc7bae5af1e4bef99c97a92a6888992
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

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