Water → 1-Benzyl-4-(pyridin-2-yl)piperidine-4-carbonitrile

HRID 324324

반응식

HRID 324324 반응식
Cl[CH2:2][CH2:3][N:4]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6]Cl.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:22]#[N:23].[OH-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:8]([N:4]1[CH2:5][CH2:6][C:21]([C:22]#[N:23])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[CH2:2][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5928N-BenzylnormechlorethamineHCID 14798Sodium HydroxideHCID 75959Pyridine-2-acetonitrile

생성물 1

HCID 227252321-Benzyl-4-(pyridin-2-yl)piperidine-4-carbonitrile수율 101.6%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매

반응 조건

온도
65 °C

실험 절차

To a mixture of N,N-bis-(2-chloroethyl)benzylamine (Szarvasi, E., Eur. J. Med. Chem. Chim. Ther. 11(2), 115-124, 1976) (60 g, 22 mmol), 2-pyridylacetonitrile (2.51 mL, 22 mmol) and tetrabutylammonium hydrogen sulfate (0.26 g, 0.7 mmol) in toluene (10 mL), sodium hydroxide solution (2.43 g in 4.86 mL H2O) was added over a 20 minute period. The reaction mixture was heated at 65° C. for 4 hours. The reaction mixture was cooled to room temperature, 10 mL of water was added and the solution partitioned between ethyl acetate (45 mL) and water. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification of the crude product by column chromatography (hexane: EtOAc, 2:3) gave 6.2 g (87 %) of the title compound as a red solid; 1H-NMR (CDCl3): δ 2.05 (d, J=13.1 Hz, 2H), 2.30 (t, J=13.2 Hz, 2H), 2.48 (t, J=13.2 Hz, 2 H), 2.97 (d, J=12.1 Hz, 2 H), 3.57 (s, 2 H), 7.19-7.27 (m, 6 H), 7.30 (d, J=7.6 Hz, 1 H), 7.60 (t, J=7.6 Hz, 1 H ), 8.58 (d, J=4.6 Hz, 1 H).

후처리

  1. additionwas added over a 20 minute period
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solution partitioned between ethyl acetate (45 mL) and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude product by column chromatography (hexane: EtOAc, 2:3)

출처 및 근거

ORD 기록
ord-b17c7038f1054d8090e85dae803eba03
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218390B1

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