Aluminium lithium hydride → HCID 59441805, compound

HRID 1014361Notes

Reaction equation

HRID 1014361 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][C:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([NH2:19])=[C:12]([O:17][CH3:18])[CH:13]=2)[CH2:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([NH2:19])=[C:12]([O:17][CH3:18])[CH:13]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 594418762-[3-(Dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine

Product 1

HCID 59441805HCID 59441805, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[3-(dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (335 mg, 1.21 mmol) in tetrahydrofuran (10 mL) was treated with lithium aluminum hydride (10 mL, 1 M in diethyl ether, 10 mmol, Aldrich). The mixture was refluxed for 16 h, cooled, quenched carefully via sequential addition of water (0.4 mL), 15% aqueous sodium hydroxide (0.4 mL), and then water (1.2 mL) again. The mixture was stirred vigorously for 1 h and then filtered through a pad of celite. The filtrate was concentrated to provide 2-[3-(dimethylamino)propyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (284 mg, 1.08 mmol, 90%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.65 (m, J=7.2, 7.2, 7.2, 7.2 Hz, 2 H), 2.11 (s, 6 H), 2.19-2.24 (m, 2 H), 2.36-2.41 (m, 2 H), 2.54 (t, J=6.0 Hz, 2 H), 2.63 (t, J=5.4 Hz, 2 H), 3.34-3.41 (m, 2 H), 3.70 (s, 3 H), 4.44 (s, 2 H), 6.28 (s, 1 H), 6.48 (s, 1 H); ESIMS (M+H)+=264.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. temperaturecooled
  3. customquenched carefully via sequential addition of water (0.4 mL), 15% aqueous sodium hydroxide (0.4 mL)
  4. filtrationfiltered through a pad of celite
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1ba6718f155a4b8f89fa144f72115668
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…