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

HRID 1275193Notes

Reaction equation

HRID 1275193 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-amineYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-aminopropyl)-4-[pyrid-2-yl]pyridinium bromide hydrobromide (0.66 g, 1.75 mmol) in 20.0 mL MeOH was added NaBH4 (0.101 g, 2.62 mmol) in small portions. The reaction mixture was stirred for 30 min and then quenched with 6M HCl solution. The solution was concentrated to 20.0 mL and basified with 50% NaOH solution to pH 12. Extracted with CHCl3 (5×30.0 mL), dried over MgSO4 and the solvent was removed to give 3-(3',6'-Dihydro-2'-H-[2,4']bipyridinyl-1'-yl)-propylamine as an oil (0.37 g, 96% yield). It is used in the next step immediately without purification.

Workup

  1. customquenched with 6M HCl solution
  2. concentrationThe solution was concentrated to 20.0 mL and basified with 50% NaOH solution to pH 12
  3. extractionExtracted with CHCl3 (5×30.0 mL)
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-5f367cb1595e426687b778579bc48f7f
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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