Dimethylformamide → HCID 14575317, compound

HRID 1085686Notes

Reaction equation

HRID 1085686 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]Cl)[CH:3]=1.[CH3:14][N:15]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].CN(C)C=[O:40]>>[C:9]([OH:40])(=[O:8])/[CH:10]=[CH:11]\[C:31]([OH:33])=[O:34].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:28]1[CH2:27][CH2:26][CH:25]([N:15]([CH3:14])[C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11961759HCID 11961759, compoundHCID 14575306HCID 14575306, compound

Product 1

HCID 14575317HCID 14575317, compoundYield 49%

Conditions

Temperature
60 °C

Procedure

A mixture of 4.4 parts of 1-chloro-3-(4-chlorobutoxy)benzene, 3.7 parts of N-methyl-N-(4-piperidinyl)-2-benzothiazolamine, 2.1 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred for 24 hours at 60° C. The reaction mixture was cooled and poured onto water. The product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromthane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (Z)-2-butenedioate salt in 2-propanone. The salt was filtered off and dried, yielding 4 parts (49%) of N-[1-[4-(3-chlorophenoxy)butyl]-4-piperidinyl]-N-methyl-2-benzothiazolamine (Z)-2-butenedioate (1:1); mp. 138.6° C. (1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. extractionThe product was extracted with methylbenzene
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromthane and methanol (97:3 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. customdried

Sources & evidence

ORD record
ord-577b5faf358d4368b7d01e42ea312e27
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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