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

HRID 84344Notes

Reaction equation

HRID 84344 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e976e46796df4de9a21e39b99775c3c6
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

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