5,6,7,8-Tetrahydroisoquinoline → 2-(13-Pyridin-3-yl-tridecyl)-5,6,7,8-tetrahydro-isoquinolinium bromide

HRID 84344노트

반응식

HRID 84344 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[CH:21]1[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:24]=[CH:23][N:22]=1>CCOCC>[Br-:1].[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N+:22]2[CH:23]=[CH:24][C:25]3[CH2:26][CH2:27][CH2:28][CH2:29][C:30]=3[CH:21]=2)[CH:16]=1

참가 물질

4

반응물 2

HCID 1190105,6,7,8-TetrahydroisoquinolineHCID 119534943-(13-Bromo-tridecyl)-pyridine

생성물 1

HCID 247813952-(13-Pyridin-3-yl-tridecyl)-5,6,7,8-tetrahydro-isoquinolinium bromide수율 62%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 5,6,7,8-tetrahydro-isoquinoline (5 ml), and the mixture was heated at 50 C overnight. The resulting residue was treated with ether, and the ether was decanted after deposition for 30′. The residue was partitioned between water and ether. The aqueous layer was washed extensively with ether, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (62%). 1HNMR (300 MHz, CDCl3, ppm), 9.22 (s, 1H), 8.90 (d, J=6.3, 1H), 8.44 (br, 2H), 7.67 (d, J=6.3, 1H), 7.55 (d, 8.1, 7.24-7.28 (m, 1H), 4.83 (t, J=7.2, 2.98-3.01 (m, 4H), 2.60 (t, J=7.8, 2H), 1.94-2.02 (m, 2H), 1.87-1.90 (m, 4H), 1.56-1.60 (m, 2H), 1.19-1.35 (br, 20H); 13CNMR, 157.87, 148.79, 146.13, 144.20, 140.68, 138.95, 138.80, 137.26, 128.08, 123.92, 61.40, 58.62, 33.30, 32.20, 31.34, 29.94, 29.82, 29.77, 29.67, 29.42, 29.36, 26.71, 26.46, 21.40, 18.81.

후처리

  1. temperaturethe mixture was heated at 50 C overnight
  2. customthe ether was decanted after deposition for 30′
  3. customThe residue was partitioned between water and ether
  4. washThe aqueous layer was washed extensively with ether
  5. extractionthe aqueous layer was extracted with chloroform
  6. customThe chloroform was removed

출처 및 근거

ORD 기록
ord-e976e46796df4de9a21e39b99775c3c6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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