Hydrochloric Acid → Hydrochloric Acid

HRID 2166014Notes

Reaction equation

HRID 2166014 reaction equation
[CH3:1][CH:2]([CH2:4][C:5](=O)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:3].C([O-])(=O)C.[NH4+].C([BH3-])#[N:17].[Na+].[ClH:20]>CO>[ClH:20].[CH3:1][CH:2]([CH2:4][CH:5]([NH2:17])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:3].[ClH:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7958Isobutyl ketoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 2

HCID 313Hydrochloric AcidHCID 230417822,6-dimethylheptan-4-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,6 -dimethyl-4 -heptanone (2.84 g, 20 mmol), ammonium acetate (15.4 g, 200 mmol) and sodium cyanoborohydride (0.93 g, 14 mmol) in methanol (75 mL) was stirred at room temperature for 20 hours. After cooling in an ice bath, the reaction mixture was acidified with concentrated HCl and concentrated under reduced pressure at 35° . The residue was partitioned between ethyl ether and water and the aqueous portion removed and made basic with 40% NaOH solution. Product was extracted into ethyl ether which was then washed with brine, dried (Na2SO4), filtered and concentrated to 1.22 g of product. Conversion to the HCl salt and recrystallation from MeOH-EtOAc gave 1.04 of pure HCl salt, mp 248°-50° dec.

Workup

  1. temperatureAfter cooling in an ice bath
  2. concentrationconcentrated under reduced pressure at 35°
  3. customThe residue was partitioned between ethyl ether and water
  4. customthe aqueous portion removed
  5. extractionProduct was extracted into ethyl ether which
  6. washwas then washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated to 1.22 g of product

Sources & evidence

ORD record
ord-fba9b53cc90b4c928ef425f2a9b3d144
Source dataset
uspto-grants-1990_07
Patent number
US04943561

Reaction notes

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