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

HRID 70022

反応式

HRID 70022 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-bcc605f83e4842cca6c7d4ea849eec77
出典データセット
uspto-grants-2014_09
特許番号
US08822513B2

関連ノート

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