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

HRID 84344

反応式

HRID 84344 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e976e46796df4de9a21e39b99775c3c6
出典データセット
uspto-grants-2014_09
特許番号
US08846937B2

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