Sodium Iodide → 6-chloro-N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]-methyl]-2-benzothiazolamine

HRID 579805Notes

Reaction equation

HRID 579805 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.Br.Br.[Cl:15][C:16]1[CH:32]=[CH:31][C:19]2[N:20]=[C:21]([NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[S:22][C:18]=2[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>O.CN(C)C(=O)C>[Cl:15][C:16]1[CH:32]=[CH:31][C:19]2[N:20]=[C:21]([NH:23][CH2:24][CH:25]3[CH2:26][CH2:27][N:28]([CH2:2][CH:3]4[O:8][C:7]5[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=5[O:5][CH2:4]4)[CH2:29][CH2:30]3)[S:22][C:18]=2[CH:17]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 212415796-chloro-N-(4-piperidinylmethyl)-2-benzothiazolamine dihydrobromide

Product 1

HCID 140489886-chloro-N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]-methyl]-2-benzothiazolamineYield 59.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1.9 parts of 2-(bromomethyl)-2,3-dihydro-1,4-benzodioxin, 3.3 parts of 6-chloro-N-(4-piperidinylmethyl)-2-benzothiazolamine dihydrobromide, 5 parts of sodium carbonate, 0.1 parts of sodium iodide and 67.5 parts of N,N-dimethylacetamide was stirred overnight at about 75° C. Water was added to the reaction mixture and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The oily residue was crystallized from a mixture of 1,1'-oxybisethane and 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.8 parts (59.8%) of 6-chloro-N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]-methyl]-2-benzothiazolamine; mp. 155.8° C. (compound 16).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe oily residue was crystallized from a mixture of 1,1'-oxybisethane and 2,2'-oxybispropane
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-8fe7211fd02c4e538dfbc26e61b2fc2b
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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