4-Methylmorpholine → (4-Phenylpiperidin-1-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 70022

Reaktionsgleichung

Reaktionsgleichung von HRID 70022
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH3:41][O:42][C:43]1[CH:44]=[C:45]([CH:49]=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[C:46](O)=[O:47]>C(Cl)Cl>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:46]([C:45]3[CH:49]=[C:50]([O:54][CH3:55])[C:51]([O:52][CH3:53])=[C:43]([O:42][CH3:41])[CH:44]=3)=[O:47])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 83573,4,5-Trimethoxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 698734-PhenylpiperidineHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 39582222(4-Phenylpiperidin-1-yl)(3,4,5-trimethoxyphenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 4-phenylpiperidine 41g (5 mmol), EDCI (6 mmol), HOBt (5.5 mmol) and NMM (6 mmol) in CH2Cl2 (50 mL) was added 3,4,5-trimethoxybenzoic acid (5.3 mmol) and stirring continued at RT for overnight. The reaction mixture was diluted with CH2Cl2 (100 mL) and sequentially washed with water, satd. NaHCO3, brine and dried over MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 1g. (57.9%). NMR (CDCl3) δ 7.35-7.21 (m, 5H), 6.66 (s, 2H), 4.84 (br, 1H), 3.95 (br, 1H), 3.88 (s, 6H), 3.86 (s, 3H), 3.20-2.87 (br, 2H), 2.85-2.74 (tt, 1H, J=3.6 Hz, J=15.6 Hz) 1.92 (br, 2H), 1.70 (br, 2H); MS (ESI) m/z 378.1 (M+Na)+.

Aufarbeitung

  1. washsequentially washed with water
  2. dry with materialNaHCO3, brine and dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customto yield a crude product, which
  5. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bcc605f83e4842cca6c7d4ea849eec77
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822513B2

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