Potassium Carbonate → 4-(4-Benzhydrylpiperazin-1-ylmethyl)-2-phenylthiazole

HRID 648212Notes

Reaction equation

Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:7][CH:8]=1.[CH:15]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:15]([N:28]1[CH2:33][CH2:32][N:31]([CH2:3][C:4]2[N:5]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:7][CH:8]=2)[CH2:30][CH2:29]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-chloromethyl-2-phenylthiazole monohydrochloride (2.46 g), 1-benzhydrylpiperazine (2.52 g) and potassium carbonate (1.4 g) in N,N-dimethylformamide (40 ml) was stirred at 70° C. for 2 hours. After the reaction mixture was poured into ice-water, it was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and then evaporated to give an oil of 4-(4-benzhydrylpiperazin-1-ylmethyl)-2-phenylthiazole, which was transformed into its hydrochloride in a conventional manner, followed by recrystallization from ethanol to obtain white crystals (2.7 g) of 4-(4-benzhydrylpiperazin-1-ylmethyl)-2-phenylthiazole dihydrochloride, mp 215°-218° C.

Workup

extractionwas extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-10ce4c5e275342acaa10d3340735c8ac
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04411900

Reaction notes

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