Propargylamine → HCID 22028626, compound

HRID 1791929Notes

Reaction equation

HRID 1791929 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](SC)=[N:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.Cl.[C:30]1([N:36]2C=CN=C2N2CCN([C@@H]3CN[C@H](C(N4CCSC4)=O)C3)CC2)C=CC=[CH:32][CH:31]=1.C(N)C#C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:31]([CH3:32])=[CH:30][N:36]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 239041PropargylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 67506234HCID 67506234, compoundHCID 67507912HCID 67507912, compound

Product 1

HCID 22028626HCID 22028626, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-Benzyloxycarbonyl-4-[(methylthio)phenyliminomethyl]piperazine [product of Example 224 (2), 2.70 g] and propargylamine (2.3 mL) were dissolved in 1-butanol (25 mL), and p-toluenesulfonic acid monohydrate (156 mg) was added thereto. The mixture was refluxed for 20 hr. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with chloroform, and the extract was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 1-benzyloxycarbonyl-4-(5-methyl-1-phenyl-2-imidazolyl)piperazine (1.82 g) as a brown oil.

Workup

  1. temperatureThe mixture was refluxed for 20 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate solution
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with chloroform
  5. washthe extract was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-042cd53d25eb4022aafcc06889b6859c
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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