Diethyl Ether → HCID 178512590, compound

HRID 2279440Notes

Reaction equation

HRID 2279440 reaction equation
Cl.[N:2]1([C:7](=[NH:9])[NH2:8])[CH:6]=[CH:5][CH:4]=N1.CCN(C(C)C)C(C)C.[O:19]1CCC(N)[CH2:21][CH2:20]1.CCOCC>CN(C=O)C>[O:19]1[CH2:20][CH2:21][CH:6]([NH:2][C:7]([NH2:8])=[NH:9])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2734672Pyrazole-1-carboxamidine monohydrochloride

Product 1

HCID 178512590HCID 178512590, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1H-pyrazole-1-carboximidamide hydrochloride (65.2 g, 445 mmol) in DMF (200 mL) at RT under nitrogen was added sequentially DIPEA (103 mL, 593 mmol) and tetrahydro-2H-pyran-4-amine (30 g, 297 mmol; CASRN 38041-19-9) and the reaction was stirred for 3 d. Et2O (100 mL) was added, and the reaction was stirred for 10 min then the reaction was allowed to settle and the ether layer was decanted. This process was repeated 3 times and a solid formed after allowing to settle for 30 min. The solid was filtered off and rinsed with Et2O and dried under high vacuum to afford 35 g, (95% purity, 78% yield) of 1-(tetrahydro-2H-pyran-4-yl)guanidine (24) as a light yellow solid: MS m/z (APCI-pos) M+1=144.1.

Workup

  1. stirringthe reaction was stirred for 10 min
  2. customthe ether layer was decanted
  3. customa solid formed
  4. waitto settle for 30 min
  5. filtrationThe solid was filtered off
  6. washrinsed with Et2O
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-97b773383de54841a194c79d3b9ba7fe
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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