Sodium Iodide → HCID 66866083, compound

HRID 253689Notes

Reaction equation

HRID 253689 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][C:13]2=[O:16])=[CH:9][CH:8]=1.[I-].[Na+].Cl.[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C>C(#N)C.C(Cl)(Cl)Cl>[ClH:20].[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][CH2:12][C:13]3=[O:16])=[CH:9][CH:8]=2)[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 115509406-(4-Bromobutyloxy)indanoneHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochloride

Product 1

HCID 66866083HCID 66866083, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(4-bromobutoxy)-indan-1-one prepared by the process described in step (1) above (100 gm, 0.282 mol, 80% purity) and sodium iodide (42 gm, 0.28 mol) in acetonitrile was refluxed for 30 minutes and then cooled to room temperature. 1-(2,3-dichlorophenyl)-piperazine hydrochloride (68 gm, 0.294 mol) and triethyl amine (77 gm, 0.761 mol) were added to the mixture and the resulting mixture was refluxed for 4-6 hr. After solvent was removed, the residue thus obtained was dissolved in chloroform, washed with water which treatment with chloroform and Hydrochloric acid gave 140 g of 6-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy]-indan-1-one hydrochloride. This on chloroform solution was basified with ammonium hydroxide to pH 9.5 and extracted with chloroform twice 2×500 ml. The combined chloroform layer was concentrated using rotavapour under reduced pressure to get a residue which on purification with methanol gave 85 gm of 6-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]-butoxy]-indan-1-one of the formula 2 which has identical characteristic of product obtained for the Example 1, step-2.

Workup

  1. customprepared by the process
  2. temperaturewas refluxed for 30 minutes
  3. temperaturethe resulting mixture was refluxed for 4-6 hr
  4. customAfter solvent was removed
  5. customthe residue thus obtained
  6. washwashed with water which treatment with chloroform and Hydrochloric acid

Sources & evidence

ORD record
ord-a1de4719d7404802b28903a7d008e2d9
Source dataset
uspto-grants-2011_01
Patent number
US07872132B2

Reaction notes

Loading…