Ethanol → (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemifumarate salt

HRID 1464927Notes

Reaction equation

[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].O.CCO.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]([CH3:24])[C:18]=2[CH:25]=1>C(OC(C)C)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]([CH3:24])[C:18]=2[CH:25]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]([CH3:24])[C:18]=2[CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemifumarate salt was prepared by dropwise addition of a half-molar amount of fumaric acid in 1:1 water:EtOH (˜0.6 M) to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in isopropyl acetate with vigorous stirring. A suspension resulted. It was heated to 60° C., held at that temperature for 1 h, and then the heat source was removed and the sample was allowed to cool to ambient temperature while stirring overnight. The suspension was filtered and the solid was washed with isopropyl acetate and dried on the filter. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemifumarate salt had an extrapolated melting onset temperature by DSC of 158° C.

Workup

customA suspension resulted
customthe heat source was removed
temperatureto cool to ambient temperature
filtrationThe suspension was filtered
washthe solid was washed with isopropyl acetate
customdried on the filter
customby DSC of 158° C.

Sources & evidence

ORD record: ord-beee34614d41493aa07d69ffe5fa09dc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999970B2

Reaction notes

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