Dibenzylamine → N,N-dibenzyl-3-chloropropan-1-amine

HRID 398254Notes

Reaction equation

HRID 398254 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][CH2:10][Cl:11].[CH2:12]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1CCCCC1>[CH2:20]([N:19]([CH2:8][CH2:9][CH2:10][Cl:11])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 18482N,N-dibenzyl-3-chloropropan-1-amineYield 53%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a stirred suspension of K2CO3 (200 g, 1.5 mole) in cyclohexane 200 mL and 1-bromo-3-chloropropane (540 gms, 3.4 mole) is added dropwise over a period of 1 h at 20° C. dibenzyl amine (442 g, 2.24 mole). After complete addition the reaction is allowed to stir for an additional 20 h. The crude reaction mixture is filtered and then washed with saturated NaCl (3×100 mL). The organic phase is extracted with 3N HCl (3×100 mL). The resulting aqueous phase, containing the desired product as the hydrochloric salt, is washed with hexanes (3×100 mL) to remove any residual BCP. The aqueous phase is subsequently basified with 50wt % NaOH and extracted with cyclohexane (3×100 mL). After solvent removal 324 g (53% yield) of the title compound was isolated as a yellow oil.

Workup

  1. additionAfter complete addition the reaction
  2. customThe crude reaction mixture
  3. filtrationis filtered
  4. washwashed with saturated NaCl (3×100 mL)
  5. extractionThe organic phase is extracted with 3N HCl (3×100 mL)
  6. additionThe resulting aqueous phase, containing the desired product as the hydrochloric salt
  7. washis washed with hexanes (3×100 mL)
  8. customto remove any residual BCP
  9. extractionextracted with cyclohexane (3×100 mL)

Sources & evidence

ORD record
ord-d1b0af979cd542229f0e9c318262ebc5
Source dataset
uspto-grants-2003_08
Patent number
US06610859B1

Reaction notes

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