Cyclopropanemethanamine → HCID 21097359, compound

HRID 2109147Notes

Reaction equation

HRID 2109147 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[NH2:9][CH2:10][CH:11]1[CH2:13][CH2:12]1>>[CH:11]1([CH2:10][NH:9][C:2]2[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=2)[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 21097359HCID 21097359, compoundYield 77%

Procedure

A solution of 500 mg (2.09 mmol) of 2-chloro-5-iodo pyridine in 1.64 g (23.1 mmol) of aminomethylcyclopropane was heated to 100° C. in a sealed tube for 48 h. The mixture was then concentrated, dissolved in EtOAc, washes with water and brine, dried with MgSO4, filtered, and concentrated. Recrystallization from hexanes provided 440 mg (1.61 mmol; 77%) of cyclopropylmethyl-(5-iodo-pyridin-2-yl)-amine. ESI MS m/z 275 [C9H11IN2+H]+.

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutiondissolved in EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-1d4391f5d3994e4e888d184e25900cd7
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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