Hydrochloric Acid → Nepicastat hydrochloride anhydrous

HRID 863074Notes

Reaction equation

HRID 863074 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]([C@H:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([F:19])=[CH:13][C:14]=3[F:18])[CH2:9]2)[C:6](=[S:20])[NH:5][CH:4]=1.[ClH:21]>CO.C(OCC)C>[ClH:21].[NH2:1][CH2:2][C:3]1[N:7]([C@H:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([F:19])=[CH:13][C:14]=3[F:18])[CH2:9]2)[C:6](=[S:20])[NH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9796181Nepicastat

Product 1

HCID 9840545Nepicastat hydrochloride anhydrous

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The (S)-5-aminomethyl-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione was dissolved in methanol and treated with 1.5 equivalents of anhydrous hydrogen chloride in ethyl ether. Removal of the solvents by co-evaporation with ethyl acetate gave (S)-5-aminomethyl-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione hydrochloride, m.p. 245° C., [aα]D25 =11.30° (c=0.5, DMSO).

Workup

  1. customRemoval of the solvents by co-evaporation with ethyl acetate

Sources & evidence

ORD record
ord-868c7464450342b8bb0425f69511f8a6
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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