Potassium Iodide → HCID 14575474, compound

HRID 1723439Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]\[C:18]([OH:20])=[O:19].[C:23]1([CH2:29][N:30]([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[C:31]2[S:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C(=O)C>[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19].[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:43]2[CH2:44][CH2:45][CH:40]([N:30]([CH2:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:31]3[S:32][C:33]4[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=4[N:35]=3)[CH2:41][CH2:42]2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4.3 parts of 1-(4-chlorobutoxy)-4-methoxybenzene, 6.6 parts of N-(phenylmethyl)-N-(4-piperidinyl)-2-benzothiazolamine (Z)-2-butenedioate(1:1), 5.3 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylacetamide was stirred overnight at 90° C. The reaction mixture was poured onto water. The product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol. The salt was filtered off and dried, yielding 5.6 parts (60%) of N-[1-[4-(4-methoxyphenoxy)butyl]-4-piperidinyl]-N-(phenylmethyl)-2-benzothiazolamine (E)-2-butenedioate(1:1); mp. 178.2° C. (181).

Workup

additionThe reaction mixture was poured onto water
extractionThe product was extracted with methylbenzene
washThe extract was washed with water
customdried
filtrationfiltered
customevaporated
filtrationThe salt was filtered off
customdried

Sources & evidence

ORD record: ord-5307883034ec4e34a05a9c766fc1a444
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04861785

Reaction notes

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