Cyclopentanecarbaldehyde → 1-(5-bromopyridin-3-yl)-N-(cyclopentylmethyl)methanamine

HRID 1472169Notes

Reaction equation

HRID 1472169 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1.[CH:10]1([CH:15]=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.[BH3-]C#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][CH2:15][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 70106CyclopentanecarbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 229922643-(Aminomethyl)-5-bromopyridine

Product 1

HCID 866983271-(5-bromopyridin-3-yl)-N-(cyclopentylmethyl)methanamineYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (5-bromopyridin-3-yl)methanamine (LVIII) (1.30 g, 5.8 mmol, 1.0 eq), cyclopentanecarbaldehyde (0.57 g, 5.8 mmol, 1.0 eq) and TEA (0.60 g, 5.8 mmol, 1.0 eq) in MeOH (15 mL) was stirred at room temperature for 2 h. Then NaBH3CN (1.98 g, 34.6 mmol, 6.0 eq) was added and the mixture was stirred at the same temperature for another 3 h. The solvent was removed under reduced pressure and the residue was diluted in water (20 mL) and extracted with DCM (10 mL×3), combined organic layers were dried over MgSO4 and concentrated in vacuo to give 1-(5-bromopyridin-3-yl)-N-(cyclopentylmethyl)methanamine (LIX) (1.23 g, 4.57 mmol, 79.3% yield) as a brown oil. ESIMS found for C12H17BrN2 m/z 269 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted in water (20 mL)
  3. extractionextracted with DCM (10 mL×3)
  4. dry with materialwere dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c936a2026950415ab2d4a85cd0a3015a
Source dataset
uspto-grants-2015_04
Patent number
US09012472B2

Reaction notes

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