HCID 67096019, compound → 2-(Morpholine-4-carbonyl)-cyclohexanone

HRID 2076113Notes

Reaction equation

HRID 2076113 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:12])[O:4]CC1>C(O)C.S(=O)(=O)(O)O.C(OCC)(=O)C>[N:13]1([C:11]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]2=[O:4])=[O:12])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

5

Reactant 1

HCID 67096019HCID 67096019, compound

Product 1

HCID 113678262-(Morpholine-4-carbonyl)-cyclohexanoneYield 35%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (1,4-dioxa-spiro[4.5]dec-6-yl)-morpholin-4-yl-methanone (59 mg, 0.23 mmol) in 60% aqueous ethanol (1.1 mL) were added 2 drops of conc. sulfuric acid (20 uL) and the mixture was heated to 80° C. for 2 h. The mixture was cooled to 20° C., diluted with ethyl acetate (20 mL) and washed with saturated aqueous sodium carbonate solution (10 mL), and with brine (10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give the title compound (17 mg, 35%) as a white solid. MS ISP (m/e): 211.9 (100) [(M+H)+].

Workup

  1. temperatureThe mixture was cooled to 20° C.
  2. washwashed with saturated aqueous sodium carbonate solution (10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-12018f6e1c6f4b09b4ab73d2100c365b
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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