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

HRID 63195

반응식

HRID 63195 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%). 1H 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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-44365af3433f41118b9e8a61ad9fb3bd
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447049B2

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