Hydrochloric Acid → 2-[4-(2-Amino-1-methyl-ethyl)-phenyl]-propylamine Dihydrochloride

HRID 48362Notes

Reaction equation

HRID 48362 reaction equation
[C:1]([CH:3]([CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:6][CH:5]=1)#[N:2].[ClH:15].CO>C1COCC1>[ClH:15].[ClH:15].[NH2:2][CH2:1][CH:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:13])[CH2:11][NH2:12])=[CH:6][CH:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 227432382-[4-(Cyano-methyl-methyl)-phenyl]-propionitrile

Product 1

HCID 227432152-[4-(2-Amino-1-methyl-ethyl)-phenyl]-propylamine DihydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-[4-(Cyano-methyl-methyl)-phenyl]-propionitrile (3.25 g, 17.7 mmol) was dissolved in anhydrous THF (30 mL). The solution was heated to reflux and a 2M THF solution of borane-methyl sulfide complex (19.5 mL, 38.9 mmol) was added dropwise. Heating at reflux was continued for 30 minutes and then allowed to cool to room temperature. An HCl saturated solution of methanol (30 mL) was slowly added until pH=2. The mixture was concentrated in vacuo, redissolved in methanol and concentrated again to provide the intermediate title compound (4.5 g, 96%). TLC and HPLC indicated the starting material had been consumed and produced a mixture of more polar products. This material was used crude in the next step without further characterization.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureHeating
  4. temperatureat reflux
  5. concentrationThe mixture was concentrated in vacuo
  6. dissolutionredissolved in methanol
  7. concentrationconcentrated again

Sources & evidence

ORD record
ord-15dfd037761243e08dcf5a0b0f78a911
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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