Ethyl Acetate → HCID 20299685, compound

HRID 1733463Notes

Reaction equation

HRID 1733463 reaction equation
[O-2].[Mg+2].[Cl:3][C:4]1[C:13]([Cl:14])=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1.[C:15]([Cl:22])(=O)[CH2:16][CH2:17][C:18]([Cl:20])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(O[CH2:35][CH3:36])(=O)C>O1CCCC1.C(Cl)Cl>[ClH:3].[ClH:20].[CH2:9]([N:10]1[CH2:35][CH2:36][C:17]2[C:16](=[C:15]([Cl:22])[C:4]([Cl:3])=[CH:5][CH:18]=2)[CH2:11]1)[CH2:8][CH2:7][CH2:6][N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:13]([Cl:14])[C:4]([Cl:3])=[CH:5][CH:6]=2)[CH2:11]1

Participants

9

Reactant 6

HCID 8857Ethyl AcetateHCID 10970Succinyl chlorideHCID 14798Sodium HydroxideHCID 123920Isoquinoline, 7,8-dichloro-1,2,3,4-tetrahydro-HCID 6850729Magnesium monoxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 20299685HCID 20299685, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.2 g. (30 mmol) of magnesium oxide in 100 ml. of methylene chloride containing 3.0 g. (15 mmol) of 7,8-dichlorotetrahydroisoquinoline free base was stirred under argon at 0° while a solution of 1.16 g. (7.5 mmol) of succinyl chloride in 25 ml. of methylene chloride was added dropwise. The mixture was stirred at room temperature overnight. It was filtered through celite and the filtrate washed with 3 N hydrochloric acid and 10% sodium hydroxide, dried and evaporated to give 1.8 g. of white solid. A suspension of 1 g. of this amide in 25 ml. of dry tetrahydrofuran was stirred at room temperature under argon while 1.0 g. of lithium aluminum hydride was added in portions over thirty minutes. It was stirred at room temperature for 5 hours and treated with 10 ml. of ethyl acetate followed by 25 ml. of 10% sodium hydroxide. The mixture was concentrated, diluted with water and extracted wsith three 50-ml portions of methylene chloride. The combined extracts were dried and treated with ethereal hydrogen chloride. The resulting precipitate was removed by filtration, washed with ether and dried to give 2,2'-butylene-bis(7,8-dichloro-1,2,3,4-tetrahydroisoquinoline)dihydrochloride having a melting point of 269°-275° C.

Workup

  1. additionA suspension of 1.2 g
  2. filtrationIt was filtered through celite
  3. washthe filtrate washed with 3 N hydrochloric acid and 10% sodium hydroxide
  4. customdried
  5. customevaporated
  6. customto give 1.8 g
  7. additionA suspension of 1 g
  8. stirringIt was stirred at room temperature for 5 hours
  9. additiontreated with 10 ml
  10. concentrationThe mixture was concentrated
  11. additiondiluted with water
  12. extractionextracted wsith three 50-ml portions of methylene chloride
  13. customThe combined extracts were dried
  14. additiontreated with ethereal hydrogen chloride
  15. customThe resulting precipitate was removed by filtration
  16. washwashed with ether
  17. customdried

Sources & evidence

ORD record
ord-1cd220d3af564971bdbf56dad2c45618
Source dataset
uspto-grants-1980_12
Patent number
US04242346

Reaction notes

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