1-(2-(Dimethylamino)ethyl)-3,4-dihydroquinolin-2(1H)-one → 2-(3,4-Dihydroquinolin-1(2h)-yl)-n,n-dimethylethanamine

HRID 1922405Notes

Reaction equation

HRID 1922405 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]([CH3:22])[CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]1=O>C1COCC1>[N:11]1([CH2:10][CH2:9][N:8]([CH3:22])[CH3:7])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 182291-(2-(Dimethylamino)ethyl)-3,4-dihydroquinolin-2(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 2305312-(3,4-Dihydroquinolin-1(2h)-yl)-n,n-dimethylethanamineYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (39.39 mL, 39.397 mmol, 1 M solution in THF) was treated with compound 2 (2.15 g, 9.849 mmol) in dry THF (25 mL) at 0° C. The reaction was brought to room temperature and stirred for over night (18 h). The reaction was quenched with water (1.5 mL), 2 N NaOH solution (1.5 mL) and water (1.5 mL). After stirring for 30 min. at room temperature, the reaction was filtered, washed with CH2Cl2 (4×20 mL). The combined organic layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98 to 5:95) to obtain compound 3 (0.95 g, 47%) as a syrup. 1H NMR (DMSO-d6) δ 6.93 (t, 1H, J=8.1 Hz), 6.83 (d, 1H, J=7.2 Hz), 6.51 (d, 1H, J=8.1 Hz), 6.43 (t, 1H, J=7.8 Hz), 3.33-3.24 (m, 4H), 2.64 (t, 2H, J=6.3 Hz), 2.36 (t, 2H, J=7.5 Hz), 2.17 (s, 6H), 1.85-1.77 (m, 2H); ES-MS (m/z, %) 205 (MH+, 22), 160 (100), 132 (65).

Workup

  1. customwas brought to room temperature
  2. customThe reaction was quenched with water (1.5 mL), 2 N NaOH solution (1.5 mL) and water (1.5 mL)
  3. stirringAfter stirring for 30 min. at room temperature
  4. filtrationthe reaction was filtered
  5. washwashed with CH2Cl2 (4×20 mL)
  6. customThe combined organic layer was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98 to 5:95)

Sources & evidence

ORD record
ord-8ed5a3187bb84926a7f08ba414de457b
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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