Sodium Carbonate → HCID 20299671, compound

HRID 1733462Notes

Reaction equation

HRID 1733462 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>C(O)C>[ClH:1].[ClH:1].[CH2:20]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[C:11]([Cl:12])[C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[C:11]([Cl:12])[C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123681,6-DibromohexaneHCID 123920Isoquinoline, 7,8-dichloro-1,2,3,4-tetrahydro-

Product 1

HCID 20299671HCID 20299671, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2.38 g. (10 mmol) of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline and 3.18 g. (30 mmol) of sodium carbonate in 50 ml. of absolute ethanol were refluxed for 5 minutes. To this suspension was added 1.22 g. (5 mmol) of 1,6-dibromohexane and the mixture refluxed overnight. The reaction was cooled and after standing for 36 hours was filtered of solid precipitate. The resulting solid was suspended in 100 ml. of ethyl acetate and treated with 1 g. of magnesium sulfate. The mixture was filtered and the filtrate treated with 10 ml. of ethereal hydrochloric acid. The resulting precipitate was removed by filtration, washed with ether and dried to give 2,2'-hexylene-bis(7,8-dichloro-1,2,3,4-tetrahydroisoquinoline)dihydrochloride having a melting point of 308°-311° C.

Workup

  1. additionA suspension of 2.38 g
  2. additionTo this suspension was added 1.22 g
  3. temperatureThe reaction was cooled
  4. filtrationwas filtered of solid precipitate
  5. additionof ethyl acetate and treated with 1 g
  6. filtrationThe mixture was filtered
  7. additionthe filtrate treated with 10 ml
  8. customThe resulting precipitate was removed by filtration
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-926a19c7b4f043448855d4e8ec151208
Source dataset
uspto-grants-1980_12
Patent number
US04242346

Reaction notes

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