Water → 8-[2-(4-Methoxyphenyl)ethyl]-1,4-dioxa-8-azaspiro[4.6]undecane

HRID 968487Notes

Reaction equation

HRID 968487 reaction equation
[O:1]1[C:5]2([CH2:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:8]2[CH2:9][CH2:10][CH2:11][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 216795911,4-Dioxa-8-azaspiro[4.6]undecane

Product 1

HCID 692829498-[2-(4-Methoxyphenyl)ethyl]-1,4-dioxa-8-azaspiro[4.6]undecaneYield 85.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of intermediate (5) (0.114 mol), 1-(2-bromoethyl)-4-methoxy-benzene (0.172 mol) and K2CO3 (0.219 mol) in ACN (200 ml) was stirred at 80° C. for 2 hours. Water was added and the mixture was extracted with DCM. The organic layer was separated, dried , filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2). The pure fractions were collected and the solvent was evaporated, yielding 28.5 g of 8-[2-(4-methoxyphenyl)ethyl]-1,4-dioxa-8-azaspiro[4.6]undecane (intermediate 6).

Workup

  1. extractionthe mixture was extracted with DCM
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0177bc7bb4844c0abf2d812eb1e53609
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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