Sodium Carbonate → N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-5,6,7-trimethoxy-2-benzothiazolamine (E)-2-butenedioate

HRID 1789513

Reaction equation

HRID 1789513 reaction equation
CS(O[CH2:6][CH:7]1[O:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][CH2:8]1)(=O)=O.[CH3:17][O:18][C:19]1[C:20]([O:38][CH3:39])=[C:21]([O:36][CH3:37])[C:22]2[S:26][C:25]([NH:27][CH2:28][CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:24][C:23]=2[CH:35]=1.[C:40](=[O:43])([O-:42])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[C:10]([OH:18])(=[O:9])/[CH:11]=[CH:13]/[C:40]([OH:42])=[O:43].[O:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9][CH2:8][CH:7]1[CH2:6][N:32]1[CH2:33][CH2:34][CH:29]([CH2:28][NH:27][C:25]2[S:26][C:22]3[C:21]([O:36][CH3:37])=[C:20]([O:38][CH3:39])[C:19]([O:18][CH3:17])=[CH:35][C:23]=3[N:24]=2)[CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 2634452,3-Dihydro-1,4-benzodioxin-2-ylmethyl methanesulfonateHCID 212416145,6,7-trimethoxy-N-(4-piperidinylmethyl)-2-benzothiazolamine

Product 1

HCID 86742980N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-5,6,7-trimethoxy-2-benzothiazolamine (E)-2-butenedioateYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2.8 parts of 2,3-dihydro-1,4-benzodioxin-2-methanol methanesulfonate (ester), 3.4 parts of 5,6,7-trimethoxy-N-(4-piperidinylmethyl)-2-benzothiazolamine, 3 parts of sodium carbonate and 67.5 parts of N,N-dimethylacetamide was stirred overnight at about 75° C. Water was added. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol and 2-propanone. The salt was filtered off and dried, yielding 3.2 parts (48.5%) of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-5,6,7-trimethoxy-2-benzothiazolamine (E)-2-butenedioate(2:3); mp. 171.6° C. (compound 26).

Workup

  1. extractionThe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

Sources & evidence

ORD record
ord-e5b173451e7142968c31ab748f8e6b09
Source dataset
uspto-grants-1987_08
Patent number
US04689330

Linked notes

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