4-Methylmorpholine → methyl (2E)-3-(2-{3-[benzoyl(3,3-diphenylpropyl)amino]propyl}phenoxy)acrylate

HRID 2389385Notes

Reaction equation

HRID 2389385 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:9][N:10]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.[C:42]([O:46][CH3:47])(=[O:45])[CH2:43][CH3:44]>CC#N.CCOC(C)=O>[C:11]([N:10]([CH2:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28]/[CH:44]=[CH:43]/[C:42]([O:46][CH3:47])=[O:45])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 11124Methyl propionateHCID 68536523N-(3,3-diphenylpropyl)-N-[3-(2-hydroxyphenyl)propyl]benzamide

Product 1

HCID 86637917methyl (2E)-3-(2-{3-[benzoyl(3,3-diphenylpropyl)amino]propyl}phenoxy)acrylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3,3-diphenylpropyl)-N-[3-(2-hydroxyphenyl)propyl]benzamide (100 mg) in MeCN (2 mL) was added NMM (2.3 mg) and methyl propionate (22.4 mg) at ambient temperature. The reaction mixture was stirred for 2 hours at the same temperature. The resulting mixture was diluted with EtOAc (15 mL) and washed successively with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-70:30) to give a methyl (2E)-3-(2-{3-[benzoyl(3,3-diphenylpropyl)amino]propyl}phenoxy)acrylate.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20-70:30)

Sources & evidence

ORD record
ord-46a738034f09431193e3a4f3076ca354
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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