1,2,3,4-Tetrahydroisoquinoline → 2-(Prop-2-yn-1-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 1163012Notes

Reaction equation

HRID 1163012 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.Br[CH2:12][C:13]#[CH:14].[Cl-].[NH4+]>CN(C=O)C>[CH2:14]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 7842Propargyl bromideHCID 25517Ammonium Chloride

Product 1

HCID 143412942-(Prop-2-yn-1-yl)-1,2,3,4-tetrahydroisoquinolineYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1,2,3,4-tetrahydro-isoquinoline (9.4 mmol) in DMF (10 ml), 3-bromo-propyne (4.5 mmol) is added at 0° C. and stirred at room temperature for 18 h. After the reaction mixture is treated with saturated ammonium chloride, the mixture is extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to a silica gel column chromatography, which is eluted with following solvents: n-hexane and n-hexane:AcOEt=1:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 91.2%, Rf=0.67 (n-hexane:AcOEt=1:5).

Workup

  1. extractionthe mixture is extracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down
  5. washis eluted with following solvents
  6. customThe solvent of the latter effluent is removed by evaporation
  7. customdried in vacuo

Sources & evidence

ORD record
ord-2f5e3851a86649378adbb7259c1958ab
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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