Benzyl Bromide → 6-Benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decan-10-one

HRID 2360712Notes

Reaction equation

HRID 2360712 reaction equation
[CH3:1][C:2]1([CH3:13])[NH:11][C:10](=[O:12])[C:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[NH:4][CH2:3]1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:14]([N:4]1[CH2:3][C:2]([CH3:13])([CH3:1])[NH:11][C:10](=[O:12])[C:5]21[CH2:9][CH2:8][CH2:7][CH2:6]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 86680334HCID 86680334, compound

Product 1

HCID 866803356-Benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decan-10-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.72 g of 8,8-dimethyl-6,9-diaza-spiro[4.5]decan-10-one in 35 ml of DMF were added 4.8 ml of benzyl bromide and 6.9 ml of Hünig's base. The reaction was stirred at r.t overnight. The precipitated product was isolated by suction and washed with DMF and EtOAc. The filtrate was concentrated and the resulting residue was dissolved in EtOAc, washed with water, dried over Na2SO4, filtered and concentrated to yield a second fraction of the product. 9.62 g (96%) of the title compound were obtained.

Workup

  1. customThe precipitated product was isolated by suction
  2. washwashed with DMF and EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe resulting residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a second fraction of the product

Sources & evidence

ORD record
ord-cc2af8a3689349c58515bf4db50d65f7
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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