1,4-Dioxa-8-azaspiro(4.5)decane → HCID 21273621, compound

HRID 842767Notes

Reaction equation

HRID 842767 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:10]1[O:19][C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[O:12][CH2:11]1>CN(C=O)C>[CH2:10]1[O:19][C:13]2([CH2:18][CH2:17][N:16]([C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[C:4]#[N:5])[CH2:15][CH2:14]2)[O:12][CH2:11]1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 678552-Fluorobenzonitrile

Product 1

HCID 21273621HCID 21273621, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-fluorobenzonitrile (2.75 g, 22.7 mmol) and 4-piperidone ethylene ketal (4.25 g, 29.7 mmol) in DMF (40 mL) was heated to 120° C. for 4 h. The resulting mixture was cooled to room temperature overnight. The solvent was removed in vacuo and the residue dissolved in ether and sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound (4). The crude product was used directly.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ether
  3. extractionThe aqueous layer was extracted with two additional portions of ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6cd2036bc7642f4968b9fc17c395982
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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