Sodium Cyanide → HCID 18768971, compound

HRID 480245Notes

Reaction equation

HRID 480245 reaction equation
[CH2:1]([N:8]([CH3:20])[CH2:9][C:10](=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:21]#[N:22].[Na+].[NH4+:24].[Cl-]>N.CO.C(Cl)Cl>[NH2:24][C:10]([CH2:9][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:20])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:21]#[N:22]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 18768982HCID 18768982, compound

Product 1

HCID 18768971HCID 18768971, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolvent2×HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

1-(Benzyl-methyl-amino)-4-phenyl-butan-2-one (2.4 g, 9.0 mmol, 1.0 equiv) was mixed in 36 mL of 2.0 M NH3 in MeOH. To the solution was added NaCN (0.484 g, 9.9 mmol, 1.1 equiv) and NH4Cl (0.528 g, 9.9 mmol, 1.1 equiv). The resulting mixture was refluxed for 2 h at which time an addition 15 mL of 2.0 M NH3 in MeOH was added and the mixture was refluxed another 4 h. Though TLC (5% MeOH in CH2Cl2) still showed the presence of the ketone, the reaction was cooled and filtered. The filtrate was concentrated and the crude product was purified by flash chromatography on SiO2 using 60% hexanes in CH2Cl2 then 1.5% MeOH to 3% MeOH was added. The desired product was isolated pure (0.561 g, 21%) as a yellow oil that crystallized upon standing at −20° C.; MS, m/z 294=M+1.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h at which time
  2. additionwas added
  3. temperaturethe mixture was refluxed another 4 h
  4. temperaturethe reaction was cooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by flash chromatography on SiO2 using 60% hexanes in CH2Cl2
  8. addition1.5% MeOH to 3% MeOH was added

Sources & evidence

ORD record
ord-65f85fecaede4f73893a2cbed3358dad
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

Loading…