Morpholine → HCID 66990889, compound

HRID 454667Notes

Reaction equation

HRID 454667 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH2:13]([O:20][C:21]1[CH:48]=[C:47]([O:49][CH2:50][CH2:51]Br)[CH:46]=[CH:45][C:22]=1[C:23]([NH:25][C:26]1[CH:38]=[C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.CC(C)=O>[CH2:13]([O:20][C:21]1[CH:48]=[C:47]([O:49][CH2:50][CH2:51][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:46]=[CH:45][C:22]=1[C:23]([NH:25][C:26]1[CH:38]=[C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 8083Morpholine2×HCID 11430Potassium Carbonate2×HCID 516892Sodium BicarbonateHCID 66990569HCID 66990569, compound

Product 1

HCID 66990889HCID 66990889, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.065 g) and morpholine (0.041 mL) were added to an acetone (3.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-4-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.094 g), followed by heating to reflux for 45 minutes. The reaction mixture was cooled to room temperature, and potassium carbonate (0.022 g) and morpholine (0.014 mL) were added thereto, followed by heating to reflux for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then water, a saturated aqueous solution of sodium bicarbonate, and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-91% chloroform/methanol] to obtain 0.059 g of tert-butyl 2-(2-(benzyloxy)-4-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 45 minutes
  3. temperatureby heating
  4. temperatureto reflux for 2 hours and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-91% chloroform/methanol]

Sources & evidence

ORD record
ord-10dbe970c2da40d0a569fcb42e85bea7
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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