Sodium Iodide → HCID 14049038, compound

HRID 579801Notes

Reaction equation

HRID 579801 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.C(O)(=O)C.[NH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>O.CN(C)C(=O)C>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 70352868N-(4-piperidinylmethyl)acetamide acetate

Product 1

HCID 14049038HCID 14049038, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 12.6 parts of 2-(bromomethyl)-2,3-dihydro-1,4-benzodioxin, 11 parts of N-(4piperidinylmethyl)acetamide acetate (1:1), 15 parts of sodium carbonate, 0.1 parts of sodium iodide and 135 parts of N,N-dimethylacetamide was stirred overnight at 75° C. The reaction mixture was poured into water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 1,1'-oxybisethane and 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.2 parts (21.0%) of N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]acetamide; mp. 137.9° C. (intermediate 89).

Workup

  1. extractionThe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe 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-ff6f10115bde426b9fb5aff66a0b7688
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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