Triethylamine → Benzyl 4-acetylpiperidine-1-carboxylate

HRID 2105521ノート

反応式

HRID 2105521 の反応式
Cl.[C:2]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])[CH3:3].CCN(CC)CC.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl.O>[C:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 441518974-Acetylpiperidinium chloride

生成物 1

HCID 19065050Benzyl 4-acetylpiperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4-Acetylpiperidine hydrochloride (4B-1, 5.0 g, 30.55 mmole) was taken up in CH2Cl2 (150 mL). To this was added Et3N (9.8 mL, 70.27 mmole) and the suspension became a solution. The mixture was cooled to 0° C. to which was added benzyl chloroformate (5.2 mL, 36.66 mmole). After the addition was complete the mixture was warmed to RT. After 18 hr the mixture was diluted with H2O. The layers were separated and the aqueous extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to afford benzyl 4-acetylpiperidine-1-carboxylate as an off-white solid (4B-2): 1H-NMR (500 MHz, CDCl3) δ 7.35 (m, 5H), 5.13 (s, 2H), 4.18 (bs, 2H), 2.88 (bs, 2H), 2.49 (m, 1H), 2.17 (s, 3H), 1.86 (bs, 2H), 1.55 (m, 2H).

後処理

  1. additionAfter the addition
  2. temperaturewas warmed to RT
  3. customThe layers were separated
  4. extractionthe aqueous extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-321701c532a447f5987470bc7e8f4451
出典データセット
uspto-grants-2009_08
特許番号
US07579355B2

反応ノート

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