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

HRID 412562Notes

Reaction equation

HRID 412562 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

4

Reactant 3

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 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).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated and to the obtained residue
  3. additionwas added a hydrogen chloride—ethanol solution and insoluble material
  4. customwas removed
  5. concentrationThe resultant mixture was concentrated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-30f9dc15549a408096500e2267402b6e
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…