2-Furancarboxylic acid → N-(2-benzothiazolyl)-N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-2-furancarboxamide monohydrochloride

HRID 579810노트

반응식

HRID 579810 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(N(CC)CC)C.[I-].[Cl:17]C1C=CC=C[N+]=1C.[O:25]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[O:28][CH2:27][CH:26]1[CH2:35][N:36]1[CH2:41][CH2:40][CH:39]([CH2:42][NH:43][C:44]2[S:45][C:46]3[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=3[N:48]=2)[CH2:38][CH2:37]1>O1CCCC1.O.ClCCl>[ClH:17].[S:45]1[C:46]2[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=2[N:48]=[C:44]1[N:43]([CH2:42][CH:39]1[CH2:38][CH2:37][N:36]([CH2:35][CH:26]2[O:25][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[O:28][CH2:27]2)[CH2:41][CH2:40]1)[C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

참가 물질

8

반응물 4

HCID 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 128556R 47243HCID 1670692-Chloro-1-methylpyridinium iodide

생성물 1

HCID 14049048N-(2-benzothiazolyl)-N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-2-furancarboxamide monohydrochloride수율 41.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred mixture of 1.12 parts of 2-furancarboxylic acid, 2.02 parts of N,N-diethylethanamine and 195 parts of dichloromethane were added 2.55 parts of 2-chloro-1-methylpyridinium iodide. Stirring was continued for 30 minutes at room temperature. A solution of 3.93 parts of N-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinylmethyl]-2-benzothiazolamine in tetrahydrofuran was added and the whole was stirred first for 1 hour at room temperature and then overnight at reflux. After cooling, the reaction mixture was poured into water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanone. The salt was filtered off and dried, yielding 2.2 parts (41.8%) of N-(2-benzothiazolyl)-N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-2-furancarboxamide monohydrochloride; mp. 217.7° C. (compound 63).

후처리

  1. stirringthe whole was stirred first for 1 hour at room temperature
  2. temperatureovernight at reflux
  3. temperatureAfter cooling
  4. extractionThe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. customdried

출처 및 근거

ORD 기록
ord-dcca251617e34ff5ada015c9e7afc180
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04749702

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