Potassium Carbonate → HCID 86746768, compound

HRID 1781405Notes

Reaction equation

HRID 1781405 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18]>C(#N)C>[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH:2]2[CH2:3][O:4][C:5]3([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]3)[O:1]2)=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 792664-Nitrophenethyl bromide

Product 1

HCID 86746768HCID 86746768, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1,4-Dioxa-8-azaspiro[4.5]-decane (18.62 g, 130 mmoles) in 50 mL of acetonitrile was stirred under argon and treated with anhydrous potassium carbonate (27.60 g, 200 mmoles). The mixture was cooled to 0° C. and 2-(4-nitrophenyl)ethylbromide (23.01 g, 100 mmoles) was added in one portion. After 10 minutes, the ice bath was removed and the reaction was stirred for 14 hrs at room temperature. The mixture was diluted with 220 mL of ethyl acetate and 200 mL of water. The aqueous phase was separated, the organic phase washed with water (3×100 mL), and brine (2×50 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to give 28.60 g (98%) of N(2-(4-nitrophenyl)ethyl-1,4-dioxa-8-azaspiro [4.5]-decane as a yellow solid.

Workup

  1. customthe ice bath was removed
  2. additionThe mixture was diluted with 220 mL of ethyl acetate and 200 mL of water
  3. customThe aqueous phase was separated
  4. washthe organic phase washed with water (3×100 mL), and brine (2×50 mL)
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-310c58e7bbc14872a5a2fd0b11d6f844
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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