Hydrochloric Acid → 1,2,3,4-Tetrahydro-isoquinolin-7-ylamine dihydrochloride

HRID 645779Notes

Reaction equation

HRID 645779 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-])=O.Cl.O.[OH-].[Na+]>CCO.O=[Pt]=O>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 426146221,2,3,4-Tetrahydro-isoquinolin-7-ylamine dihydrochlorideYield 92.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

7-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (2) from Example 1, is placed in a Parr shaker bottle (15.0 g, 69.9 mmol) dissolved in 95% EtOH (100 mL), and to the Parr shaker bottle is added concentrated HCl (10 mL), water (25 mL), and PtO2 (0.5 g). The mixture is hydrogenated at 50 psi until no further drop in pressure was observed (about 4 hours). The yellowish suspension is filtered through Celite and evaporated to dryness to afford a yellowish solid which is made basic with 10% NaOH solution (adequate care is exercised in catalyst disposal). Extraction of the basic solution with CHCl3 (three times), followed by drying over anhydrous Na2SO4 and evaporation of the solvent, yields a reddish yellow solid (9.54 g, 92.2%): mp=110-112. 7-Amino-1,2,3,4-tetrahydroisoquinoline dihydrochloride (3) is recrystallized from aqueous MeOH as buff colored needles, mp=290° C.

Workup

  1. custom(about 4 hours)
  2. filtrationThe yellowish suspension is filtered through Celite
  3. customevaporated to dryness
  4. customto afford a yellowish solid which
  5. extractionExtraction of the basic solution with CHCl3 (three times)
  6. dry with materialby drying over anhydrous Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-5fba5ec5296e418fb2b1cc6e1bcdbc3d
Source dataset
uspto-grants-2010_04
Patent number
US07705017B2

Reaction notes

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