2-butyl-2-phenylhexanenitrile → β,β-Dibutylbenzeneethanamine

HRID 1092725Notes

Reaction equation

HRID 1092725 reaction equation
[CH2:1]([C:5]([CH2:14][CH2:15][CH2:16][CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]#[N:7])[CH2:2][CH2:3][CH3:4]>C(O)C>[NH2:7][CH2:6][C:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:1][CH2:2][CH2:3][CH3:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 2367002-butyl-2-phenylhexanenitrile

Product 1

HCID 54021135β,β-Dibutylbenzeneethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

α,α-Dibutyl-benzeneacetonitrile ((2), 7.0 gm; 0.0237 mol) is dissolved in borane-THF complex (1.1 equiv.) at room temperature for 18 hours. Once reaction is complete, ethanol (50 ml) is added, and the reaction is evaporated to dryness. Once dry, the residue is suspended in 100 ml 1M HCl, and the suspension is evaporated to dryness on a rotary evaporator. This procedure is repeated three times. After the final evaporation, the white residue is dissolved in 1M NaOH (100 ml), and extracted with diethyl ether (2×150 ml). The extracts are combined, dried with Na2SO4, filtered and evaporated to dryness to yield 1-amino-2,2-dibutyl-2-phenylethane (3), wt=6.4 gm (90%).

Workup

  1. customOnce reaction
  2. customthe reaction is evaporated to dryness
  3. customOnce dry
  4. customthe suspension is evaporated to dryness on a rotary evaporator
  5. customAfter the final evaporation
  6. dissolutionthe white residue is dissolved in 1M NaOH (100 ml)
  7. extractionextracted with diethyl ether (2×150 ml)
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-1dff5fdb3d304ccfb4d3be27ce5529d0
Source dataset
uspto-grants-2012_03
Patent number
US08129531B2

Reaction notes

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