Sodium Iodide → N-methyl-N-(prop-2-ynyl)-5,6,7,8-tetrahydroquinolin-8-amine

HRID 628684Notes

Reaction equation

HRID 628684 reaction equation
[CH3:1][NH:2][CH:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.[CH2:13](Br)[C:14]#[CH:15].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[CH3:1][N:2]([CH2:15][C:14]#[CH:13])[CH:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 58985336N-methyl-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 59176406N-methyl-N-(prop-2-ynyl)-5,6,7,8-tetrahydroquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-5,6,7,8-tetrahydroquinolin-8-amine, 5, (0.50 g, 3.08 mmol) in THF (15 mL) was added propargyl bromide (0.28 mL, 3.08 mmol), sodium iodide (0.05 g, 0.31 mmol) and sodium carbonate (0.98 g, 9.24 mmol). The reaction mixture was stirred at room temperature for 3 h. The mixture was diluted with water, extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude solid was used without further purification: 1H NMR (d6-DMSO) δ 8.30 (d, J=4.4 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.13 (dd, J=8.0, 5.2 Hz, 1H), 3.74 (dd, J=4.8, 4.8 Hz, 1H), 3.47 (ddd, J=16.8, 2.4, 2.4 Hz, 2H), 3.06 (s, 1H), 2.80-2.60 (m, 2H), 2.12 (s, 3H), 2.12-1.87 (m, 2H), 1.74-1.68 (m, 1H), 1.62-1.55 (m, 1H); ESI+ MS: m/z (rel intensity) 201.1 (100, [M+H]+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude solid was used without further purification

Sources & evidence

ORD record
ord-ce4b9e0c926e49f788d70c9b5e94f33a
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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