HCID 67478938, compound → HCID 60922454, compound

HRID 472433Notes

Reaction equation

HRID 472433 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][N:6]([CH3:11])[S:7]([CH3:10])(=[O:9])=[O:8])#[N:2]>[Pd].N.CO>[NH2:2][CH2:1][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH2:5][N:6]([CH3:11])[S:7]([CH3:10])(=[O:9])=[O:8]

Participants

5

Reactant 1

HCID 67478938HCID 67478938, compound

Product 1

HCID 60922454HCID 60922454, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

156 b) To a Paar bottle (250 mL) was added 10% palladium on carbon (50% wet)(1.1 g, 0.52 mmol) followed by a solution of N-(2-cyano-benzyl)-N-methyl-methanesulfonamide (1.28 g, 5.71 mmol) in 7 M of ammonia in methanol (50 mL). The mixture was degassed and charged with Hydrogen (50 psi). The mixture was shaken on a Paar apparatus until adsorption of hydrogen ceased. The mixture was degassed and kept under an atmosphere of nitrogen. The mixture was filtered through a plug of diatomaceous earth, rinsed with dichloromethane and evaporated. N-(2-Aminomethyl-benzyl)-N-methyl-methanesulfonamide was isolated as tan viscous oil (1.28 g, 98%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.41 (d, J=7.4 Hz, 1H), 7.36-7.24 (m, 3H), 4.40 (s, 2H), 3.99 (s, 2H), 2.89 (s, 3H), 2.72 (s, 3H). MS=229 (MH)+.

Workup

  1. customThe mixture was degassed
  2. additioncharged with Hydrogen (50 psi)
  3. customThe mixture was degassed
  4. filtrationThe mixture was filtered through a plug of diatomaceous earth
  5. washrinsed with dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-4a62b4df23ef43cf8ecc7def621435c5
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

Loading…