Chloroform → 7-[1-(2-Hydroxyethyl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine dihydrochloride

Reaction equation

C(OC([NH:8][C:9]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]3[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][OH:38])[CH2:32][CH2:31]3)=[CH:23][CH:24]=2)[CH2:19]1)=[N:10]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)(Cl)[Cl:47]>>[ClH:47].[ClH:47].[OH:38][CH2:37][CH2:36][N:33]1[CH2:34][CH2:35][CH:30]([CH2:29][O:28][C:22]2[CH:21]=[C:20]3[C:25]([CH2:26][CH2:27][N:18]([C:9]([NH2:10])=[NH:8])[CH2:19]3)=[CH:24][CH:23]=2)[CH2:31][CH2:32]1

Participants

Reactant 3

HCID 6212Chloroform

HCID 6422Trifluoroacetic acid

HCID 69696807N,N'-Di-tert-butoxycarbonyl-7-[1-(2-hydroxyethyl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine

Product 1

HCID 185365577-[1-(2-Hydroxyethyl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine dihydrochloride

Procedure

To a solution of N,N′-di-tert-butoxycarbonyl-7-[1-(2-hydroxyethyl)-piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine (60 mg) in chloroform (0.6 ml)solution was added trifluoroacetic acid (0.3 ml), and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was evaporated and to the obtained residue was added a hydrogen chloride—ethanol solution and insoluble material was removed. The resultant mixture was concentrated and dried under reduced pressure to give the title compound (40 mg).