Hydrochloric Acid → HCID 89815638, compound

HRID 2172322Notes

Reaction equation

HRID 2172322 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23]3)[CH2:4][CH2:3]1.Cl.O1CCOCC1>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([F:16])([F:15])[F:17])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH2:20][CH2:21][NH:22][CH2:23]3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89815457HCID 89815457, compound

Product 1

HCID 89815638HCID 89815638, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 5-(2-(4-methylpiperazin-1-yl)-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.680 g, 3.53 mmol) in 4 mL THF was treated with HCl 4N in dioxane (8.83 ml, 35.3 mmol) and was heated to reflux with a heat gun. The reaction mixture was allowed to stir for an additional hour then the reaction mixture was concentrated. Purification of the resulting residue by reverse phase column chromatography [RediSep Gold C18 150 g, 5-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 5-(2-(4-methylpiperazin-1-yl)-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (1.031 g, 2.75 mmol,) as a light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux with a heat gun
  3. concentrationthe reaction mixture was concentrated
  4. customPurification of the resulting residue by reverse phase column chromatography [RediSep Gold C18 150 g, 5-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)]

Sources & evidence

ORD record
ord-d49ac74265914770b5217663f1925855
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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