Sodium Iodide → 4-(1-Pyrrolidinylmethyl)-2-{4-[3-(1-pyrrolidinyl)propoxy]phenyl}-1,3-thiazole

HRID 1710748Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17]Cl)=[CH:10][CH:9]=2)[S:6][CH:7]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.ClCCl>[N:19]1([CH2:2][C:3]2[N:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:10][CH:9]=3)[S:6][CH:7]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-thiazole ax72 (250 mg, 0.83 mmole, 1 eq) and pyrrolidine (0.3 ml, 3.6 mmol, 4.4 eq) is dissolved in acetonitrile (10 ml). Potassium carbonate (0.5 g, 3.6 mmole, 4.4 eq) and sodium iodide (25 mg, 0.17 mmole, 0.2 eq) are added. The solution is heated at 90° C. in a sealed tube for 48 h. After cooling, the solution is taken up in dichloromethane, washed with water and dried over magnesium sulfate. The crude material is purified by chromatography on silicagel (gradient: dichloromethane/methanol/ammonia 95:4.5:0.5 to 90:9:1) to provide 0.31 g of 4-(1-pyrrolidinylmethyl)-2-{4-[3-(1-pyrrolidinyl)propoxy]phenyl}-1,3-thiazole 73 as a brown oil.

Workup

temperatureAfter cooling
washwashed with water
dry with materialdried over magnesium sulfate
customThe crude material is purified by chromatography on silicagel (gradient: dichloromethane/methanol/ammonia 95:4.5:0.5 to 90:9:1)

Sources & evidence

ORD record: ord-0b50e36126264d7ea704d35d178501c6
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

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