Aluminium lithium hydride → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzylamine

HRID 586076Notes

Reaction equation

HRID 586076 reaction equation
[CH:1]12[N:8]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:5]12[N:8]([C:9]3[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[C:11]([Cl:17])[CH:10]=3)[CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 223376884-(8-Azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzonitrile

Product 1

HCID 223376344-(8-Azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(8-Azabicyclo[3.2.1]oct-8-yl)-2-chlorobenzonitrile in THF (50 mL) was treated with solid LAH (0.47 g, 12 mmol) at 0° C. portionwise. The mixture was heated at reflux for 1 hour, allowed to cool to 0° C., and quenched by addition of (Na2SO4 10H2O). The mixture was stirred for 30 minutes, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 5% to 10% MeOH/CH2Cl2 to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.27 (d, 1H, J=8.6 Hz), 6.74 (d, 1H, J=2.4 Hz), 6.70 (dd, 1H, J=8.6, 2.4 Hz), 4.16 (bs, 2H), 3.65 (s, 2H), 2.05 (bs, 2H), 1.97 (m, 2H), 1.88-1.65 (m, 5H), 1.40 (m, 1H), 1.23 (m, 2H); MS (ESI) 234 (M−NH2)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customquenched by addition of (Na2SO4 10H2O)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-678353cde4584063a4e02f88b90b8265
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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