Ethylamine hydrochloride → 2-(6-Bromo-3,4-dihydroquinolin-1(2H)-yl)-N-ethylethanamine

HRID 1922489Notes

Reaction equation

HRID 1922489 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13]I)[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:22]([NH2:24])[CH3:23]>C(#N)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][NH:24][CH2:22][CH3:23])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 573433966-Bromo-1-(2-iodoethyl)-1,2,3,4-tetrahydroquinoline2×

Product 1

HCID 573434002-(6-Bromo-3,4-dihydroquinolin-1(2H)-yl)-N-ethylethanamineYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6-bromo-1-(2-iodoethyl)-1,2,3,4-tetrahydroquinoline (compound 3, 100 mg, 0.273 mmol) in acetonitrile (4.75 mL) and water (0.25 mL) in a 20 mL pressure vessel fitted with a stir-bar is treated with potassium carbonate (0.378 g, 2.73 mmol) and ethylamine hydrochloride (0.223 g, 2.73 mmol) and the sealed vessel stirred at 70° C. overnight. After 18 hours the mixture was partitioned between CH2Cl2 (50 mL) and water (10 mL) and transferred to a separatory funnel. The organic layer was separated and the aqueous layer extracted further with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give a yellow residue. The residue was purified on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane to yield a yellow oil/residue, 4 (55 mg, 71.1%). 1H-NMR (CDCl3) δ 7.09 (dd, 1H, J=8.7, 2.4 Hz), 7.06-7.01 (m, 1H), 6.51 (d, 1H, J=8.7), 3.36 (t, 2H, J=6.8 Hz), 3.29 (t, 2H, J=5.5 Hz), 2.82 (t, 2H, J=6.8 Hz), 2.80-2.65 (2×m, 4H), 1.96-1.88 (m, 2H), 1.11 (t, 3H, J=7.1 Hz).

Workup

  1. customAfter 18 hours the mixture was partitioned between CH2Cl2 (50 mL) and water (10 mL)
  2. customtransferred to a separatory funnel
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted further with CH2Cl2
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow residue
  10. customThe residue was purified on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane

Sources & evidence

ORD record
ord-3fd98828051f4f5eba924a8f54bba2dc
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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