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

HRID 1785786Notes

Reaction equation

HRID 1785786 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([O-])([O-])=O.[K+].[K+].O>CN1C(=O)CCC1>[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 962WaterHCID 11430Potassium CarbonateHCID 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 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 4-fluorobenzoate (6.0 mL, 41 mmol), 1,4-dioxa-8-azaspiro(4,5)decane (13.5 mL, 102 mmol), and K2CO3 (5.7g, 41 mmol) in NMP (35 mL) was stirred at 150° C. for 4 hours, cooled to room temperature, treated with water (0.5 L) and filtered. The filter cake was washed with water and dried briefly. The crude product was triturated with hexane, filtered, and dried under vacuum to provide the desired product. MS (DCI) m/e 292 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filter cake was washed with water
  4. customdried briefly
  5. customThe crude product was triturated with hexane
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e8e457236b264b25b3fc98e7a3146bc6
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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