Methanol → 1-Methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1690240Notes

Reaction equation

HRID 1690240 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.CO>C1COCC1.Cl.CCOCC>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 2

HCID 887MethanolHCID 155921-Methylisoquinoline

Product 1

HCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineYield 77%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-methylisoquinoline (133 μL, 1.0 mmol) in THF under nitrogen was added dropwise a solution of LiBEt3H in THF (1.0M, 2.2 mL, 2.2 mmol) to give a yellow solution. After stirring 1.5 h, MeOH (1.2 mL) was added dropwise to produce a clear colorless solution, which was then diluted with 1M aq. HCl and ether. The aqueous layer was extracted three times with ether, then made basic (pH 14) by addition of 1M aq. NaOH. The aqueous layer was extracted five times with DCM, dried over MgSO4, filtered and concentrated to give the desired product in 77% yield, which was used without further purification. LC/MS (10-99%) M/Z: M+1 obs=148.3; tR=0.62 min.

Workup

  1. customto give a yellow solution
  2. customto produce a clear colorless solution, which
  3. extractionThe aqueous layer was extracted three times with ether
  4. additionby addition of 1M aq. NaOH
  5. extractionThe aqueous layer was extracted five times with DCM
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-63fcddb7f29742e5a7d5980d4ac445a6
Source dataset
uspto-grants-2012_04
Patent number
US08153655B2

Reaction notes

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