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

HRID 1789517Notes

Reaction equation

HRID 1789517 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3c011460876e45b6b5bb44988893edcf
Source dataset
uspto-grants-1987_08
Patent number
US04689330

Reaction notes

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