Hydrochloric Acid → (2S)-Methyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine dihydrochloride

HRID 420779Notes

Reaction equation

HRID 420779 reaction equation
[ClH:1].[CH3:2][NH:3][C@H:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:14]2[C:15]([CH3:21])=[N:16][N:17]([CH3:20])[C:18]=2[CH3:19])[CH2:5]1>CCOCC>[ClH:1].[ClH:1].[CH3:2][NH:3][C@H:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:14]2[C:15]([CH3:21])=[N:16][N:17]([CH3:20])[C:18]=2[CH3:19])[CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24875363(2S)-Methyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine

Product 1

HCID 66659177(2S)-Methyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine dihydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

HCl (6.0 mL, 4 M solution in dioxane, 24.03 mmol) was dropwise added to a suspension of (2S)-methyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine (2.16 g, 8.01 mmol) in Et2O (10 mL). The reaction mixture was stirred at room temperature for 2.5 h and then the solvent was concentrated off. The resulting solid was suspended in Et2O (25 mL) and concentrated, in order to remove excess of HCl. This operation was done for three times, to give 2.42 g of the title product (Rf=0.3 (AcOEt/MeOH/Et3N 20:3:2), white solid, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-ae5bec858a884d429924015847743abe
Source dataset
uspto-grants-2012_01
Patent number
US08097641B2

Reaction notes

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