Methanol → 2-Phenylbutane-1,2-diamine

HRID 2227452Notes

Reaction equation

HRID 2227452 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH2:11][CH3:12])[C:9]#[N:10].CO>CCOCC.C(Cl)Cl>[C:13]1([C:8]([NH2:7])([CH2:11][CH3:12])[CH2:9][NH2:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 167944572-Amino-2-phenylbutanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 211492-Phenylbutane-1,2-diamineYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (LAH, 7.0 g) in 250 mL of ether is added dropwise a solution of the compound of step 1(10.0 g) in 10 mL of ether at −70° C. The reaction mixture is stirred at −60° C. to −70° C. until TLC (10% MeOH in CH2Cl2) shows the disappearance of the starting material. The excess LAH is destroyed by cautious addition of a saturated aqueous Na2SO4 solution. The resulting mixture is filtered and solid is washed with EtOAc. The filtrate is dried over Na2SO4 and concentrated under vacuum to give 8.3 g of the title compound as clear oil.

Workup

  1. customThe excess LAH is destroyed by cautious addition of a saturated aqueous Na2SO4 solution
  2. filtrationThe resulting mixture is filtered
  3. washsolid is washed with EtOAc
  4. dry with materialThe filtrate is dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d6ee337e164742759ca44d393570b26f
Source dataset
uspto-grants-2002_07
Patent number
US06413982B1

Reaction notes

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