Hydrochloric Acid → HCID 13557557, compound

HRID 1583410Notes

Reaction equation

HRID 1583410 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10](=O)[CH3:11])[CH:3]=1.C([BH3-])#[N:14].[Na+].C([O-])(=O)C.[NH4+].Cl>CO>[CH3:11][CH:10]([NH2:14])[CH2:9][CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 202606074-(Pyridin-3-yl)butan-2-one--hydrogen chloride (1/1)

Product 1

HCID 13557557HCID 13557557, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 12.0 g of 4-(3-pyridinyl)-2-butanone hydrochloride, 3.38 g of sodium cyanoborohydride, and 42.78 g of ammonium acetate in 200 ml of methanol was stirred at room temperature for 2.5 days, acidified with dilute hydrochloric acid, and concentrated. The residue was dissolved in aqueous potassium carbonate solution and was extracted with dichloromethane. The residue obtained after evaporation of the dichloromethane was distilled to give 6.5 g (80%) of α-methyl-3-pyridinepropanamine, bp 126°-148° C./0.3 mm. The picrate was crystallized from methanol-ether; mp 146°-148° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in aqueous potassium carbonate solution
  3. extractionwas extracted with dichloromethane
  4. customThe residue obtained
  5. customafter evaporation of the dichloromethane
  6. distillationwas distilled

Sources & evidence

ORD record
ord-91812548dccf4c799188e5f7f90faa97
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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