HCID 86677132, compound → HCID 68650232, compound

HRID 1771879Notes

Reaction equation

HRID 1771879 reaction equation
[N:1]([C@@H:4]([CH3:16])[CH2:5][C:6]1[CH:7]=[C:8]([N:13]([CH3:15])[CH3:14])[CH:9]=[CH:10][C:11]=1[CH3:12])=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][C@@H:4]([CH3:16])[CH2:5][C:6]1[CH:7]=[C:8]([N:13]([CH3:15])[CH3:14])[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 1

HCID 86677132HCID 86677132, compound

Product 1

HCID 68650232HCID 68650232, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[(2S)-2-azidopropyl]-4-methylphenyl}-N,N-dimethylamine (71 mg, 0.325 mmol) in 10 mL of EtOAc was added Pd/C (30 mg of 10% Pd) and the mixture was hydrogenated under hydrogen balloon for 1 h. The catalyst was removed by filtration through celite, then passed through silicagel plug eluting first with EtOAc (10 mL), then MeOH/EtOAc/NH4OH 20:75:5 (20 mL). The fraction with product was evaporated to give N-{3-[(2S)-2-aminopropyl]-4-methylphenyl}-N,N-dimethylamine (53 mg, 85%) as pale yellow oil. ESI-MS: m/z (MH+) 193.1. 1H NMR (300 MHz, CDCl3): δ 7.02 (m, 1H), 6.57 (m, 2H), 3.16 (m, 1H), 2.90 (s, 6H), 2.44-2.74 (m, 2H), 2.22 (s, 3H), 1.48 (s, 2H), 1.14 (d, J=6.42 Hz, 3H).

Workup

  1. customfor 1 h
  2. customThe catalyst was removed by filtration through celite
  3. washeluting first with EtOAc (10 mL)
  4. customThe fraction with product was evaporated

Sources & evidence

ORD record
ord-353f38e04db44d40a2530e390b155694
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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