Potassium Iodide → HCID 14575472, compound

HRID 1085687Notes

Reaction equation

HRID 1085687 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.C(O)(=O)/C=C\C(O)=O.[CH2:21]([N:23]([CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[C:24]1[S:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1)[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[CH2:21]([N:23]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[CH2:35][CH2:34]1)[C:24]1[S:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1)[CH3:22]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 177796Benzene, 1-(3-bromopropoxy)-4-methyl-HCID 14575280HCID 14575280, compound

Product 1

HCID 14575472HCID 14575472, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.04 parts of 1-(3-bromopropoxy)-4-methylbenzene, 7.54 parts of N-ethyl-N-(4-piperidinyl)-2-benzothiazolamine (Z)-2-butenedioate (1:1), 5.3 parts of sodium carbonate, 0.1 parts of potassium iodide and 180 parts of N,N-dimethylformamide was stirred and heated overnight at 60° C. The reaction mixture was poured onto water and the product was extracted with methylbenzene. The extract was washed three times with water, dried, filtered and evaporated. The residue was crystallized from 2-propanol, yielding 6 parts (75%) of N-ethyl-N-[1-[3-(4-methylphenoxy)propyl]-4-piperidinyl]-2-benzothiazolamine; mp. 101.0° C. (123).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with methylbenzene
  3. washThe extract was washed three times with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-42c0e10926ae43c59c0cb1beb3e02810
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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