Water → HCID 54352100, compound

HRID 1656144Notes

Reaction equation

HRID 1656144 reaction equation
Cl[CH2:2][C@@H:3]([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]#[N:8])[CH3:4].[C-]#N.[Na+].[OH2:19].CCCC[CH2:24][CH3:25]>CS(C)=O>[C:24]([NH:8][C@@H:7]1[CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:3]([CH3:4])[CH2:2]1)(=[O:19])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 8929Sodium CyanideHCID 22848101HCID 22848101, compound

Product 1

HCID 54352100HCID 54352100, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To 112.31 g (0.504 mol) of (S)-N-(1-chloro-2-propyl)-N-cyanomethylbenzylamine or the the mixture of compounds from step 1c, in 500 mL of anhdrous DMSO under nitrogen atmosphere was added 37.10 g (0.757 mol) of sodium cyanide. The reaction was stirred at 60° C. for 21 hours, slurried with water and extracted with ether. The extract was washed with brine, dried over magnesium sulfate, concentrated, and the residue chromatographed on silica gel, eluting with ethyl acetate:hexane in 1:4, 1:2, and 1:1 ratios to give 81.47 g (75.5% yield) of the title compound. MS M/Z: 231, 233 (M+NH4). NMR (CDCl3) δ: 1.41 (3H, d, J=6.5 Hz), 2.57 (1H, dd, J=6.5, J=16.5 Hz), 2.66 (1H, dd, J=6.5, J=16.5 Hz), 3.34 (1H, sextet, J=6.5 Hz), 3.48 (2H, s), 3.81 (2H, s), 7.36 (5H, m).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue chromatographed on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-25d699ab457f48dca58e5957486cec32
Source dataset
uspto-grants-1993_10
Patent number
US05252747

Reaction notes

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