Hydrochloric Acid → (2S)-5-(1,3,5Trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-ylamine dihydrochloride

HRID 420783Notes

Reaction equation

HRID 420783 reaction equation
[ClH:1].[CH3:2][N:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][C@H:13]([NH2:19])[CH2:14]3)[C:5]([CH3:20])=[N:4]1>CCOCC>[ClH:1].[ClH:1].[CH3:2][N:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][C@H:13]([NH2:19])[CH2:14]3)[C:5]([CH3:20])=[N:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24989528(2S)-5-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 66658896(2S)-5-(1,3,5Trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-ylamine dihydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

HCl (0.42 mL, 4 M solution in dioxane, 1.688 mmol) was dropwise added to a suspension of (2S)-5-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine (0.143 g, 0.563 mmol) in Et2O (5 mL). The reaction mixture was stirred at room temperature for 3 h and then the solvent was concentrated off. The resulting solid was suspended in Et2O (10 mL) and concentrated, in order to remove excess of HCl. This operation was repeated for three times, to give 0.150 g of the title product (Rf=0.2 (AcOEt/MeOH/Et3N 20:3:2), white solid, 91% yield).

Workup

  1. concentrationthe solvent was concentrated off
  2. concentrationconcentrated, in order
  3. customto remove excess of HCl

Sources & evidence

ORD record
ord-8691bf71b25c4f93bcd81b8956b1ec66
Source dataset
uspto-grants-2012_01
Patent number
US08097641B2

Reaction notes

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