1-Bromo-3-chloropropane → N,N-Di-tert-butyl-3-chloropropan-1-amine

HRID 2181376Notes

Reaction equation

HRID 2181376 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][CH2:10][Cl:11].[C:12]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])([CH3:14])[CH3:13]>C1CCCCC1>[C:12]([N:16]([CH2:8][CH2:9][CH2:10][Cl:11])[C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 30889N-(1,1-Dimethylethyl)-2-methyl-2-propanamine

Product 1

HCID 22486067N,N-Di-tert-butyl-3-chloropropan-1-amineYield 51%

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 20C di-t-butyl amine (289 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 50 wt % NaOH and extracted with cyclohexane (3×100 mL). After solvent removal 234 g (51% yield) of the title compound is 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-b1d0cbe3c76e4c9396e23df13699b9f1
Source dataset
uspto-grants-2005_05
Patent number
US06891019B2

Reaction notes

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