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

HRID 2085432Notes

Reaction equation

HRID 2085432 reaction equation
[BH4-].[Na+].Br.[Br-].[NH2:5][CH2:6][CH2:7][CH2:8][N+:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:11][CH:10]=1>CO>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][CH2:6][NH2:5])[CH2:10][CH:11]=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-amineYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (2 g, 53 mmol) in small portions was added to a solution of 1-(3-aminopropyl)-4-[2-pyridyl]pyridinium bromide hydrobromide (6 g, 16 mmol) in MeOH (150 mL) at 0-5° C. over a period of 2 h. The reaction mixture was stirred overnight at room temperature and then the solvent was evaporated. The residue was suspended in ether (200 mL) and treated with aqueous 50% NaOH solution (100 mL). The ether layer was separated and the aqueous layer was extracted with additional ether (2×50 mL). The combined ether extracts were dried over potassium carbonate and the solvent was removed, giving 3-(3′,6′-dihydro-2′-H-[2,4′]bipyridinyl-1′-yl)propylamine (3.48 g) as an oil. The crude product was used in the next step immediately without further purification.

Workup

  1. customthe solvent was evaporated
  2. additiontreated with aqueous 50% NaOH solution (100 mL)
  3. customThe ether layer was separated
  4. extractionthe aqueous layer was extracted with additional 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-c84be2d76a924e0696cb2800a438b28f
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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