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

HRID 1858456Notes

Reaction equation

HRID 1858456 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) δ 0.24 (m, 2 H), 0.35 (m, 2H), 1.30 (d, J=7 Hz, 6 H), 2.10 (tt, J=12, 3 Hz, 1 H), 3.23 (heptet, J=7 Hz, 1 H), 3.77 (s, 2 H), 7.21 (s, 1 H). Mass spectrum: (M+H)+ =197.

Workup

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

Sources & evidence

ORD record
ord-4051cf4445984ecdbf9f0322e70a8546
Source dataset
uspto-grants-2000_11
Patent number
US06150530

Reaction notes

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