Cyclopropylamine → 2-Isopropyl-4-(((N-cyclopropyl)amino)methyl)thiazole

HRID 1939785Notes

Reaction equation

HRID 1939785 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([CH:9]([CH3:11])[CH3:10])[S:7][CH:8]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[CH:9]([C:6]1[S:7][CH:8]=[C:4]([CH2:3][NH:15][CH:12]2[CH2:14][CH2:13]2)[N:5]=1)([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 187588464-(Chloromethyl)-2-(propan-2-yl)-1,3-thiazole--hydrogen chloride (1/1)

Product 1

HCID 107504142-Isopropyl-4-(((N-cyclopropyl)amino)methyl)thiazoleYield 19%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.8 g (10.2 mmol) of 4-(chloromethyl)-2-isopropylthiazole hydrochloride in 10 ml of chloroform was added dropwise with stirring to 10 ml of cyclopropylamine. The resulting solution was stirred at ambient temperature for 16 h, concentrated in vacuo, and purified by silica gel chromatography using 5% methanol in chloroform to provide 0.39 g (19%) of the desired compound. 1H NMR (DMSO-d6) δ0.24 (m, 2H), 0.35 (m, 2H), 1.30 (d, J=7 Hz, 6H), 2.10 (tt, J=12, 3 Hz, 1H), 3.23 (heptet, J=7 Hz, 1H), 3.77 (s, 2H), 7.21 (s, 1H). Mass spectrum: (M+H)+ =197.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-688cab509d2b475fab2ec976d8e50841
Source dataset
uspto-grants-1997_12
Patent number
US05696270

Reaction notes

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