Sodium Iodide → HCID 9907463, compound

HRID 651341Notes

Reaction equation

HRID 651341 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[C:20]1([CH2:19][N:14]2[CH2:13][CH2:12][C:11]3([N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:8][NH:9][C:10]3=[O:17])[CH2:16][CH2:15]2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 68451-ChloromethylnaphthaleneHCID 11430Potassium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one

Product 1

HCID 9907463HCID 9907463, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (185.04 g, 0.76 mol) was suspended in 2-butanone (3600 ml). 1-(Chloromethyl)naphthalene (169.21 g, 0.91 mol), dry potassium carbonate (345.42 g, 2.50 mol) and sodium iodide (113.91 g, 0.76 mol) were added and the mixture was heated at reflux temperature for 24 h. The solvent was evaporated in vacuo and the remainder was distributed between water (2000 ml) and diethyl ether (2000 ml). The formed precipitate was collected by filtration, washed successively with water (800 ml), toluene (600 ml) and ice cold acetone (2×200 ml) and dried affording the title compound as a powder (191.20 g, 68% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 24 h
  3. customThe solvent was evaporated in vacuo
  4. filtrationThe formed precipitate was collected by filtration
  5. washwashed successively with water (800 ml), toluene (600 ml) and ice cold acetone (2×200 ml)
  6. customdried

Sources & evidence

ORD record
ord-3aa220c90d6b44b39d468753d3618e1c
Source dataset
uspto-grants-2001_08
Patent number
US06277991B1

Reaction notes

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