Hydrochloric Acid → N-[3-(Aminomethyl)-5-(1-methylethyl)phenyl]acetamide

HRID 2071037Notes

Reaction equation

HRID 2071037 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1)#[N:2].[BH4-].[Na+].Cl>CCO>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68669811HCID 68669811, compound

Product 1

HCID 59569807N-[3-(Aminomethyl)-5-(1-methylethyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 91.9 mg (0.459 mmol) of N-(3-cyano-5-(prop-1-en-2-yl)phenyl)acetamide and 110 mg (0.466 mmol) of CoCl2.6H2O in 3 mL of EtOH at 50° C. was added 118 mg of NaBH4 in 2 portions. After 3 h 45 min., 5 N HCl was added to a pH=1, and the mixture was concentrated. Ammonium hydroxide was added to a pH=9, and H2O was also added. The aqueous layer was extracted with the extract of (40 mL CHCl3: 5 mL of MeOH: 5 mL of H2O) (2×). The combined extracts were dried over Na2SO4, filtered, and concentrated to provide the crude N-(3-(aminomethyl)-5-isopropylphenyl)acetamide which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. additionAmmonium hydroxide was added to a pH=9, and H2O
  3. additionwas also added
  4. extractionThe aqueous layer was extracted with the
  5. extractionextract of (40 mL CHCl3: 5 mL of MeOH: 5 mL of H2O) (2×)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-464417e3069b4d969c411529081c76f4
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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