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

HRID 1861172Notes

Reaction equation

HRID 1861172 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. 1 H 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-bc6d1f859d3d4a6997c9813cac00a5b9
Source dataset
uspto-grants-2003_03
Patent number
US06531610B1

Reaction notes

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