1-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)cycloheptane-carbonitrile → 1-Phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one

HRID 991459Notes

Reaction equation

HRID 991459 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]3([C:19]#N)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:8][CH2:7]2)[N:5](C2C=CC=CC=2)[CH2:4][NH:3]1.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[C:27]1([N:5]2[C:6]3([CH2:7][CH2:8][N:9]([C:12]4([C:19]5[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=5)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)[CH2:10][CH2:11]3)[C:2](=[O:1])[NH:3][CH2:4]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 158711771-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)cycloheptane-carbonitrileHCID 178418255HCID 178418255, compound

Product 1

HCID 98224551-Phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-oneYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)cycloheptane-carbonitrile (323 mg, 0.916 mmol) in THF (6 ml) was added phenylmagnesium bromide (3M solution in diethyl ether, 3.05 ml, 9.16 mmol) at room temperature. Then the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was poured into ice water, then extracted with CH2Cl2. The extracts combined were dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (CH2Cl2/MeOH:10/1 to give 70.5 mg (19.1%) of title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe extracts combined were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (CH2Cl2/MeOH

Sources & evidence

ORD record
ord-7f4d8eff4f5b49e385c256de1b9611da
Source dataset
uspto-grants-2002_10
Patent number
US06465478B1

Reaction notes

Loading…