Water → N-cyclopropylpyridin-4-amine

HRID 2291510Notes

Reaction equation

HRID 2291510 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-2a2872fd006c4e8bb5a377e0011025ce
Source dataset
uspto-grants-1989_01
Patent number
US04797149

Reaction notes

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