Hydrochloric Acid → HCID 23316449, compound

HRID 1982396Notes

Reaction equation

HRID 1982396 reaction equation
FC(F)(F)C(O)=O.[BH4-].[Na+].[N+:10]([C:13]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][C:14]=1[C:15]#[N:16])([O-:12])=[O:11].Cl>O1CCCC1>[N+:10]([C:13]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][C:14]=1[CH2:15][NH2:16])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 3194902-Nitro-5-(piperidin-1-yl)benzonitrileHCID 4311764Sodium borohydride

Product 1

HCID 23316449HCID 23316449, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture consisting of 2.4 ml of trifluoroacetic acid and 10 ml of tetrahydrofuran was added dropwise to a suspension of 1.2 g of sodium borohydride in 6 ml of tetrahydrofuran under ice-cooling. To the resulting mixture was added a solution of 1.48 g of 2-nitro-5-piperidinobenzonitrile which was prepared in Reference Example 1-(a) in 15 ml of tetrahydrofuran, followed by stirring overnight. 20 ml of a 10% hydrochloric acid aqueous solution was added dropwise to the reaction mixture under ice-cooling, and the resulting mixture was heat-refluxed for 1 hour. The tetrahydrofuran was removed from the reaction mixture by distillation under reduced pressure. The aqueous layer was washed with chloroform, neutralized with sodium hydrogencarbonate and extracted with chloroform. The extracted layer was washed with water, dried and concentrated to dryness under reduced pressure. Purification of the residue by silica gel chromatography gave 1.28 g of 2-nitro-5-piperidinobenzylamine as an oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturethe resulting mixture was heat-refluxed for 1 hour
  4. customThe tetrahydrofuran was removed from the reaction mixture by distillation under reduced pressure
  5. washThe aqueous layer was washed with chloroform
  6. extractionextracted with chloroform
  7. washThe extracted layer was washed with water
  8. customdried
  9. concentrationconcentrated to dryness under reduced pressure
  10. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-18b27797ab33462a820cb4e58d97c3f7
Source dataset
uspto-grants-1986_06
Patent number
US04596806

Reaction notes

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