Triethylamine → Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

HRID 1929403Notes

Reaction equation

HRID 1929403 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C(=O)C>[O:13]1[C:17]2([CH2:22][CH2:21][N:20]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 12717439Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Ethyl 4-fluorobenzoate (11.65 g, 69.3 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (9.92 g, 69.3 mmol), and triethylamine (9.66 mL, 69.3 mmol) in N,N-dimethylacetamide (80 mL) were stirred at 80° C. for 24 hours. The reaction was cooled, poured into ethyl acetate, washed with 3× water and brine, and concentrated to afford the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with 3× water and brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5ec619838252497eaa6255c64b7ebc87
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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