L-Pyroglutamic Acid → (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine pyroglutamate salt

HRID 1464934Notes

Reaction equation

HRID 1464934 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]([CH3:21])[C:15]=2[CH:22]=1>C(OCC)(=O)C>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]([CH3:21])[C:15]=2[CH:22]=1

Participants

4

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 11658860Lorcaserin

Product 1

HCID 86702388(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine pyroglutamate salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine pyroglutamate salt was prepared by combining one equivalent of pyroglutamic acid with (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in ethyl acetate at 60° C. then cooling slowly and stirring overnight. The resulting white solid was isolated by filtration and dried. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine pyroglutamate salt had an extrapolated melting onset temperature by DSC of about 139° C.

Workup

  1. customat 60° C.
  2. temperaturethen cooling slowly
  3. customThe resulting white solid was isolated by filtration
  4. customdried
  5. customby DSC of about 139° C.

Sources & evidence

ORD record
ord-748eab108e5e454b8e6abfb7448b8270
Source dataset
uspto-grants-2015_04
Patent number
US08999970B2

Reaction notes

Loading…