Sodium Iodide → 1-[(4-Chlorophenyl)(phenyl)methyl]-1,4-diazepane

HRID 1032966

Reaction equation

HRID 1032966 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6](Cl)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[I-].[Na+].[NH:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(O)(C)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]([N:18]2[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 68163Hexahydro-1,4-diazepineHCID 2415844-Chlorobenzhydryl chloride

Product 1

HCID 27627031-[(4-Chlorophenyl)(phenyl)methyl]-1,4-diazepane

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chlorobenzhydryl chloride (5.32 g, 22.4 mmol), isopropanol (80 ml) and sodium iodide (3.41 g, 22.8 mmol) was stirred at room temperature for 30 minutes. Thereto was added homopiperazine (11.2 g, 112 mmol), and the mixture was stirred at 95° C. for 18 hours. The solvent was distilled off, and the concentrate was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The thus-obtained crude product was used for the next reaction without purification.

Workup

  1. stirringthe mixture was stirred at 95° C. for 18 hours
  2. distillationThe solvent was distilled off
  3. additionthe concentrate was poured into a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe thus-obtained crude product
  9. customwas used for the next reaction without purification

Sources & evidence

ORD record
ord-677349ed45c5437db8e0af3f48f1ebbf
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Linked notes

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