Sulfuric Acid → 6,8-Dichloro-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 870150Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]([CH3:15])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)O.S(=O)(=O)(O)O.[OH-].[Na+]>ClCCl>[Cl:20][C:18]1[CH:17]=[C:16]2[C:3](=[C:2]([Cl:1])[CH:19]=1)[CH2:4][N:5]([CH3:15])[CH2:6][CH:7]2[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-phenylethanol (3.4 g, 11.00 mmol, 1.00 equiv) in dichloromethane (15 mL). This was followed by the addition of sulfuric acid (15 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 2 h at 0° C. in a water/ice bath. The pH value of the solution was adjusted to 7 with 1M sodium hydroxide. The resulting solution was extracted with ethyl acetate (3×60 mL) and the combined organic layers dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with petroleum ether:ethyl acetate (80:1). This resulted in 1.6 g (50%) of the title compound as a colorless oil.

Workup

customInto a 100-mL 3-necked round-bottom flask, was placed
stirringThe resulting solution was stirred for 2 h at 0° C. in a water/ice bath
extractionThe resulting solution was extracted with ethyl acetate (3×60 mL)
dry with materialthe combined organic layers dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-b78f25b8cee346398902bf230b65466d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969377B2

Reaction notes

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