Dimethylformamide → N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N-methyl-2-benzothiazolamine

HRID 1789516Notes

Reaction equation

HRID 1789516 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]([CH2:18][NH:19][C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:14][CH2:13]1.[CH3:29]N(C)C=O.[H-].[Na+].IC>O>[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]([CH2:18][N:19]([CH3:29])[C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128556R 47243

Product 1

HCID 14049018N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N-methyl-2-benzothiazolamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 11.85 parts of N-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinylmethyl]-2-benzothiazolamine in 72 parts of N,N-dimethylformamide were added portionwise 1.5 parts of a sodium hydride dispersion 50%. Upon completion, stirring was continued for 30 minutes. A solution of 4.6 parts of iodomethane in 18 parts of N,N-dimethylformamide was added dropwise. The whole was stirred overnight at room temperature. The reaction mixture was poured into water and the product was extracted twice with 4-methyl-2-pentanone. The combined organic layers were dried, filtered and evaporated. The residue was separated by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The first fraction was collected and the eluent was evaporated. The residue was crystallized from a mixture of acetonitrile and 1,1'-oxybisethane, yielding 1 part of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N-methyl-2-benzothiazolamine; mp. 125.4° C. (compound 62).

Workup

  1. stirringThe whole was stirred overnight at room temperature
  2. extractionthe product was extracted twice with 4-methyl-2-pentanone
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was separated by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  8. customThe first fraction was collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of acetonitrile and 1,1'-oxybisethane

Sources & evidence

ORD record
ord-8448f9365305453fbaf740a187d7bdeb
Source dataset
uspto-grants-1987_08
Patent number
US04689330

Reaction notes

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