Water → N-cyclopropylpyridin-4-amine

HRID 1649702Notes

Reaction equation

HRID 1649702 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.O>CN(C=O)C>[CH:15]1([NH:18][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 122884-ChloropyridineHCID 69828Cyclopropylamine

Product 1

HCID 19854218N-cyclopropylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a magnetically stirred, 25° C. solution of 2.3 g (0.006 mol) of product of Step A and 0.71 g (0.007 mol) of triethylamine in 40 ml of DMF was added dropwise 0.38 g (0.007 mol) of cyclopropylamine. After 18 hours the reaction mixture was poured into H2O and extracted with diethyl ether. The ether phase was washed with H2O, and dried (MgSO4). The dry ether phase was concentrated in vacuo to 1.95 g of a brown solid. The crude was recrystallized from hexane/EtOAc affording 1.2 g (50%) of product as a beige solid; mp 111°-112° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether phase was washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationThe dry ether phase was concentrated in vacuo to 1.95 g of a brown solid
  5. customThe crude was recrystallized from hexane/EtOAc affording 1.2 g (50%) of product as a beige solid

Sources & evidence

ORD record
ord-15b07f6687274474a60864e8a80251c3
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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