1,2,3,4-Tetrahydroisoquinoline → 2-[4-(4-Butyl-phenyl)-but-3-ynyl]-5,6,7,8-tetrahydro-isoquinolinium bromide

HRID 84339Notes

Reaction equation

HRID 84339 reaction equation
[Br:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][NH:17]1>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([C:5]#[C:4][CH2:3][CH2:2][N+:17]2[CH:18]=[CH:19][C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C:25]=3[CH:16]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 593163501-(4-Bromo-but-1-ynyl)-4-butyl-benzene

Product 1

HCID 237260742-[4-(4-Butyl-phenyl)-but-3-ynyl]-5,6,7,8-tetrahydro-isoquinolinium bromideYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Bromo-but-1-ynyl)-4-butyl-benzene (1 mmol) was added to a solution of tetrahyroisoquinoline (2 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in a vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no tetrahyroisoquinoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (68%). 1HNMR (300 MHz, CDCl3, ppm), 9.30 (s, 1H), 9.04 (d, J=6.3, 2H), 7.62 (d, J=6.3, 1H), 7.18 (d, J=8.4, 2H), 7.06 (d, J=8.4, 2H), 5.10 (t, J=6.0, 3.21 (t, J=6.0, 2H), 2.94-2.96 (m, 2H), 2.56 (t, J=8.1, 2H), 1.81-1.87 (m, 2H), 1.49-1.56 (m, 2H), 1.27-1.34 (m, 2H), 0.89 (t, J=7.2, 3H); 13CNMR, 158.51, 144.59, 143.95, 140.93, 138.61, 131.55, 128.71, 127.57, 119.46, 85.97, 83.23, 59.58, 35.86, 33.69, 31.01, 26.70, 23.12, 22.63, 21.37, 14.28.

Workup

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in a vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no tetrahyroisoquinoline
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

Sources & evidence

ORD record
ord-d71cca4094284e39bd92c7c5e1706c0a
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

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