2-Chlorobenzyl chloride → HCID 57682471, compound

HRID 888756Notes

Reaction equation

HRID 888756 reaction equation
[N:1]12[CH2:9][CH2:8][CH2:7][C:6]1=[N:5][CH2:4][CH2:3][CH2:2]2.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][N:5]1[CH:6]2[N:1]([CH2:9][CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 119062-Chlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 21226445Aluminium lithium hydride

Product 1

HCID 57682471HCID 57682471, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 ml three-necked flask, 5 g (0.04 mol) of 1,5-diazabicyclo[4.3.0]non-5-ene are dissolved in 100 ml of tetrahydrofuran, and at room temperature 6.48 g (0.04 mol) of 2-chlorobenzyl chloride are slowly added with stirring. A colourless suspension is formed which is stirred overnight. The suspension is then filtered, the salt isolated by filtration is washed, and the washed salt is suspended in 100 ml of tetrahydrofuran. Added to this suspension in portions is 0.76 g (0.02 mol) of lithium aluminium hydride. After the end of the addition, the reaction mixture is stirred at room temperature overnight. It is then cooled to 0° C. and, dropwise, 0.8 g of water, then 0.8 g of 10% strength sodium hydroxide solution and a further 2.4 g of water are added. The resulting suspension is stirred at room temperature for 30 minutes and then filtered. The filter cake is washed with tetrahydrofuran and the combined organic phases are dried and concentrated on a rotary evaporator. This gives 7.15 g of 5-(2-chlorobenzyl)-1,5-diazabicyclo[4.3.0]nonane as a colourless oil.

Workup

  1. customA colourless suspension is formed which
  2. stirringis stirred overnight
  3. filtrationThe suspension is then filtered
  4. customthe salt isolated by filtration
  5. washis washed
  6. additionAdded to this suspension in portions
  7. additionAfter the end of the addition
  8. stirringthe reaction mixture is stirred at room temperature overnight
  9. stirringThe resulting suspension is stirred at room temperature for 30 minutes
  10. filtrationfiltered
  11. washThe filter cake is washed with tetrahydrofuran
  12. customthe combined organic phases are dried
  13. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-69c5a7356392466d8a9f203a4abafb86
Source dataset
uspto-grants-2012_08
Patent number
US08252784B2

Reaction notes

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