Benzyl Chloride → HCID 67165685, compound

HRID 552342Notes

Reaction equation

HRID 552342 reaction equation
[CH2:1]([C@@H:8]1[NH:12][C:11]2([CH2:17][CH2:16][N:15]([C:18](=[O:26])[C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)[NH:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH4+].[Cl-]>C1COCC1>[CH2:30]([N:10]1[C:11]2([CH2:17][CH2:16][N:15]([C:18](=[O:26])[C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[CH2:14][CH2:13]2)[NH:12][C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:27])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67165776HCID 67165776, compound

Product 1

HCID 67165685HCID 67165685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(S)-benzyl-8-(4-chlorobenzoyl)-1,4,8-triazaspiro[4,5-]-decan-2-one (2.1 g, 5.5 mmol) in 20 mL of dry THF there was added sodium hydride (130 mg, 5.5 mmol) at 0° C. and under a blanket of nitrogen. Following stirring over a period of 1 h at 0° C., benzyl chloride (760 mg, 6.0 mmol) was slowly added dropwise, and the mixture was allowed to warm up to RT and then heated under reflux over a period of 4 d. Following the addition of an aqueous saturated NH4Cl solution (30 mL), the reaction mixture was isolated by filtration, the filtrate was extracted with EE (3×20 mL), the combined organic phases were dried over Na2SO4, and the solvent was removed. Further purification was carried out by column chromatography. The product 1,3-(S)-dibenzyl-8-(4-chlorobenzoyl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained as a yellow oil in a yield of 2.62 g (99%).

Workup

  1. temperatureto warm up to RT
  2. temperatureheated
  3. temperatureunder reflux over a period of 4 d
  4. customthe reaction mixture was isolated by filtration
  5. extractionthe filtrate was extracted with EE (3×20 mL)
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customthe solvent was removed
  8. customFurther purification

Sources & evidence

ORD record
ord-f90268cb53354c31aa2ee10f95130d56
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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