2-Chlorobenzothiazole → HCID 14049023, compound

HRID 579808Notes

Reaction equation

HRID 579808 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH:18]([CH3:20])[NH2:19])[CH2:14][CH2:13]1.Cl[C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1.[O-2:31].[Ca+2].CN(C)C(=[O:37])C>>[C:6]([OH:1])(=[O:37])[C:5]([OH:4])=[O:31].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([CH:18]([NH:19][C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH3:20])[CH2:16][CH2:17]1

Participants

5

Reactant 4

HCID 119872-ChlorobenzothiazoleHCID 31374DimethylacetamideHCID 6850728CalciumoxideHCID 21241578HCID 21241578, compound

Product 1

HCID 14049023HCID 14049023, compoundYield 39.7%

Conditions

Temperature
140 °C

Procedure

A mixture of 4 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-α-methyl-4-piperidinemethanamine, 2.7 parts of 2-chlorobenzothiazole, 1.5 parts of calcium oxide and 18 parts of N,N-dimethylacetamide was stirred for 4 hours at 140° C. The whole was filtered and to the filtrate was added 4-methyl-2-pentanone. The whole was washed with water, 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 ethanedioate salt in ethanol and acetonitrile. The salt was filtered off and dried, yielding 3.4 parts (39.7%) of N-[1-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]ethyl]-2-benzothiazolamine ethanedioate(1:2); mp. 179.6° C. (compound 60).

Workup

  1. filtrationThe whole was filtered and to the filtrate
  2. additionwas added 4-methyl-2-pentanone
  3. washThe whole was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. customdried

Sources & evidence

ORD record
ord-f2989e672b9a4f47803eabe5fe29ec8e
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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