Diisopropylamine → N,N-Diisopropyl-3-cyano-3-phenylpropanamide

HRID 428340Notes

Reaction equation

HRID 428340 reaction equation
[C:1]([CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][C:5]([OH:7])=O)#[N:2].[OH-].[K+].C(Cl)(=O)C(Cl)=O.[CH:22]([NH:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C1C=CC=CC=1.C(OCC)C>[CH:22]([N:25]([CH:26]([CH3:28])[CH3:27])[C:5](=[O:7])[CH2:4][CH:3]([C:1]#[N:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 14797Potassium HydroxideHCID 65578Oxalyl chlorideHCID 111946253-Cyano-3-phenylpropanoic acid

Product 1

HCID 18357355N,N-Diisopropyl-3-cyano-3-phenylpropanamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

3-Cyano-3-phenylpropanoic acid (67.7 g, 0.389 mol) was dissolved in 2-PrOH. To the filtered acid solution was carefully added KOH (18.4 g, 0.33 mol) dissolved in 2-PrOH (200 mL), diethyl ether (100 mL) was added and the precipitate was filtered off. The dried acid salt (51.9 g, 0.24 mol) was suspended in benzene (400 mL) and oxalyl chloride was carefully added. The reaction mixture was stirred at 80° C. for 2 hours. The solvent was evaporated and the residue was co-evaporated twice with benzene. The brown oil was dissolved in benzene (200 mL) and cooled in an ice-bath. A solution of diisopropylamine (82 g, 0.81 mol) in benzene (200 mL) was added to the stirred reaction mixture during 45 min. The mixture was left to slowly warm up to room temperature overnight. The solvent was evaporated and the residue was taken up in diethyl ether and 1 M HCl. The organic phase was washed once with water, once with 1 M NaOH, again with water, dried (Na2SO4) and the solvent evaporated to afford the title compound as a dark brown oil, 41.7 g (41%): 1H NMR (CDCl3) δ1.07 (d, 3H), 1.17 (d, 3H), 1.36 (m, 6H), 2.77 (m, 1H), 2.97 (m, 1H), 3,51 (br, 1H), 3.81 (m, 1H), 4.50 (dd, 1H), 7.39 (m, 5H).

Workup

  1. filtrationthe precipitate was filtered off
  2. customThe solvent was evaporated
  3. dissolutionThe brown oil was dissolved in benzene (200 mL)
  4. temperaturecooled in an ice-bath
  5. waitThe mixture was left
  6. temperatureto slowly warm up to room temperature overnight
  7. customThe solvent was evaporated
  8. washThe organic phase was washed once with water, once with 1 M NaOH, again with water
  9. dry with materialdried (Na2SO4)
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-d8017a2b428647b08537eab8b2e6e3fc
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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