Morpholine → HCID 66722555, compound

HRID 1639539Notes

Reaction equation

HRID 1639539 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22](Br)=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CC(P(C(C)(C)C)C1C(C2C=CC=CC=2)=CC=CC=1)(C)C.[CH3:53][C:54]([CH3:57])([O-:56])[CH3:55].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:21][C:10]=1[C:11]([O:56][C:54]([CH3:57])([CH3:55])[CH3:53])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 8083MorpholineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoateHCID 23676156Sodium t-butoxide

Product 2

HCID 66722555HCID 66722555, compoundHCID 66722830HCID 66722830, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg (1.26 mmol) of benzyl 2-benzyloxy-5-bromobenzoate, 132 μL (132 mg, 1.5 mmol) of morpholine, 6 mg of palladium(II) acetate, 8.5 mg of (2-biphenyl)di-tert-butylphosphine, and 170 mg, 1.76 mmol) of sodium tert-butoxide in 3 mL of toluene is heated at 85° C. for 2 hrs. The reaction mixture is then diluted with ethyl acetate, washed with brine and dried over Na2SO4. After removal of solvent by rotoevaporation, the crude product is chromatographed to give 121 mg (0.30 mmol) of benzyl 2-benzyloxy-5-(morpholin-4-yl)benzoate and 72 mg (0.20 mmol) of tert-butyl 2-benzyloxy-5-(morpholin-4-yl)benzoate.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customAfter removal of solvent by rotoevaporation
  4. customthe crude product is chromatographed

Sources & evidence

ORD record
ord-3396e0a0cd4846ab871146092063be3d
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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