Potassium Carbonate → 6-Octyl-1,2,3,4-tetrahydroisoquinoline

HRID 710311Notes

Reaction equation

HRID 710311 reaction equation
FC(F)(F)C([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:11]=2)[CH2:6]1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:15]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][NH:5][CH2:14][CH2:13]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866617662,2,2-Trifluoro-1-(6-octyl-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Product 1

HCID 667264996-Octyl-1,2,3,4-tetrahydroisoquinolineYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Step D (0.1 g; 0.29 mmol) and K2CO3 (0.04 g; 0.29 mmol) in 50% aqueous MeOH (5 ml) was refluxed for 3 h, under N2, then cooled to room temperature. The organic solvent was removed under reduced pressure and the residue was diluted to 15 ml with Et2O, washed with, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give a title compound (0.07 g; 98%), as a colourless syrup. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.9 Hz); 1.26 (m, 10H); 1.56 (m, 2H); 2.52 (tr, 3H, J=6.9 Hz); 2.71-2.8 (m, 2H); 3.08-3.16 (m, 2H); 3.96-4.01 (m, 2H); 6.8-7.07 (m, 3H).

Workup

  1. temperaturewas refluxed for 3 h, under N2
  2. customThe organic solvent was removed under reduced pressure
  3. additionthe residue was diluted to 15 ml with Et2O
  4. washwashed with, H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1d5c3f3e5c164e939ff123eacf54bfd7
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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