5,6,7,8-Tetrahydroisoquinoline → HCID 86640071, compound

HRID 1925446Notes

Reaction equation

HRID 1925446 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13]Br.[CH:15]1[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=[CH:17][N:16]=1>C(#N)C>[Br-:1].[Br-:1].[CH2:2]([N+:16]1[CH:17]=[CH:18][C:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C:24]=2[CH:15]=1)[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][N+:16]1[CH:17]=[CH:18][C:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C:24]=2[CH:15]=1

Participants

4

Reactant 2

HCID 1190105,6,7,8-TetrahydroisoquinolineHCID 58338516HCID 58338516, compound

Product 1

HCID 86640071HCID 86640071, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis-cis-1,12-Dibromo-dodeca-5,7-diene was added to a solution of 5,6,7,8-tetrahydro-isoquinoline (3 mmol) in acetonitrile and the solution refluxed for 24 hours. The acetonitrile was removed in vacuum and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no isoquinoline left in the aqueous layer. The resulting aqueous solution of the product was lyophilized to yield the pure product. (75%). 1HNMR (300 MHz, D2O, ppm), 8.30 (s, 2H), 8.19 (d, J=6.6, 2H), 7.50 (d, J=6.3, 2H), 6.09-6.16 (m, 2H), 5.28-5.36 (m, 2H), 4.27 (t, J=7.2, 4H), 2.29-2.82 (br, 4H), 2.67-2.74 (br, 4H), 2.02 (q, J=7.2, 4H), 1.81 (p, J=7.2, 4H), 1.62-1.69 (m, 8H), 1.22 (p, J=7.2, 4H). CNMR158.82, 143.10, 139.60, 138.96, 132.28, 127.92, 124.09, 60.82, 49.13, 30.07, 29.35, 26.32, 26.20, 25.43, 21.01.

Workup

  1. temperaturethe solution refluxed for 24 hours
  2. customThe acetonitrile was removed in vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no isoquinoline
  5. waitleft in the aqueous layer
  6. customto yield the pure product

Sources & evidence

ORD record
ord-beb17d2a9b164e3f8aedae967da611bc
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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