Ethanone, 2-chloro-1,2-diphenyl- → (RS)-7-(2-Oxo-1,2-diphenyl-ethyl)-1-phenyl-1,7-diaza-spiro[3.5]nonan-2-one

HRID 1952681

Reaction equation

HRID 1952681 reaction equation
Cl[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:17]1([N:23]2[C:26]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH2:25][C:24]2=[O:32])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>CC(=O)CC>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]([N:29]1[CH2:28][CH2:27][C:26]2([N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:24](=[O:32])[CH2:25]2)[CH2:31][CH2:30]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 95343Ethanone, 2-chloro-1,2-diphenyl-HCID 516892Sodium BicarbonateHCID 109768741-Phenyl-1,7-diazaspiro[3.5]nonan-2-one

Product 1

HCID 23298863(RS)-7-(2-Oxo-1,2-diphenyl-ethyl)-1-phenyl-1,7-diaza-spiro[3.5]nonan-2-oneYield 89.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 2-chloro-1,2-diphenyl-ethanone (0.23 g, 1 mmol), 1-phenyl-1,7-diazaspiro[3.5]nonan-2-one (0.2 g, 0.9 mmol) and sodium bicarbonate (0.23 g) in 2-butanone was boiled for 4 h with stirring. The mixture was cooled, the solvent was removed in vacuo and the residue was purified by chromatography on silica gel with ethylacetate/hexane (1:2) to yield 0.33 g (87%) of the title compound. MS: m/e=411.3 (M+H+).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by chromatography on silica gel with ethylacetate/hexane (1:2)

Sources & evidence

ORD record
ord-d8a2ac0baf9f454597b26e4908411bd8
Source dataset
uspto-grants-2000_09
Patent number
US06113527

Linked notes

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