Sodium borohydride → 3-(3',6'-Dihydro-[2,4'-bipyridin]-1'(2'H)-yl)propan-1-amine

HRID 1977803Notes

Reaction equation

HRID 1977803 reaction equation
Br.[Br-].[NH2:3][CH2:4][CH2:5][CH2:6][N+:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.[BH4-].[Na+]>CO>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][CH2:4][NH2:3])[CH2:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 696993801-(3-Aminopropyl)-4-[2-pyridyl]pyridinium bromide hydrobromide

Product 1

HCID 184761423-(3',6'-Dihydro-[2,4'-bipyridin]-1'(2'H)-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-aminopropyl)-4-[2-pyridyl]pyridinium bromide hydrobromide (6 g, 16 mmol) in MeOH (150 mL) at 0° C. was added NaBH4 (2 g, 53 mmol) in small portions over a period of 2 h. The reaction mixture was stirred overnight at room temperature and the solvent was evaporated. The residue was suspended in ether (200 mL) and treated with 50% NaOH solution (100 mL). The ether layer was separated and the aqueous layer was extracted with ether (2×50 mL). The combined ether extracts were dried over potassium carbonate and the solvent was removed to give 3-(3′,6′-dihydro-2′-H-[2,4′]bipyridinyl-1′-yl)-propylamine as an oil. It was immediately used in the next step without purification.

Workup

  1. customthe solvent was evaporated
  2. additiontreated with 50% NaOH solution (100 mL)
  3. customThe ether layer was separated
  4. extractionthe aqueous layer was extracted with ether (2×50 mL)
  5. dry with materialThe combined ether extracts were dried over potassium carbonate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-ad4b4896df9b4d35a36f28e43eeeb6af
Source dataset
uspto-grants-2001_05
Patent number
US06235759B1

Reaction notes

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