Potassium Iodide → N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-2-benzothiazolamine

HRID 1085688

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=O)=O.Br.Br.[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[S:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[N:29]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][N:18]2[CH2:19][CH2:20][CH:21]([NH:24][C:25]3[S:26][C:27]4[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=4[N:29]=3)[CH2:22][CH2:23]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2.3 parts of [2-(4-methoxyphenyl)ethyl] methanesulfonate, 4 parts of N-(4-piperidinyl)-2-benzothiazolamine dihydrobromide, 5.3 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide was stirred overnight at 70° C. The reaction mixture was poured onto water and the product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.5 parts (41%) of N-[1-[2-(4-methoxyphenyl)-ethyl]-4-piperidinyl]-2-benzothiazolamine; mp. 142.5° C. (178).

Workup

additionThe reaction mixture was poured onto water
extractionthe product was extracted with methylbenzene
washThe extract was washed with water
customdried
filtrationfiltered
customevaporated
customThe residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane
filtrationThe product was filtered off
customdried

Sources & evidence

ORD record: ord-2b99b01b32df4e46b27ab0a7d10c157d
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05010198

Linked notes

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