HCID 15917481, compound → HCID 15917483, compound

HRID 1758531Notes

Reaction equation

HRID 1758531 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:29]=[CH:28][C:11]2[CH2:12][C:13]3([O:27][C:10]=2[CH:9]=1)[C:22]1[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:16][N:15]([C:23](=O)[CH2:24][CH3:25])[CH2:14]3>O1CCCC1.CCOCC>[ClH:7].[Cl:7][C:8]1[CH:29]=[CH:28][C:11]2[CH2:12][C:13]3([O:27][C:10]=2[CH:9]=1)[C:22]1[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:16][N:15]([CH2:23][CH2:24][CH3:25])[CH2:14]3

Participants

5

Reactant 2

HCID 15917481HCID 15917481, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15917483HCID 15917483, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a refluxing suspension of lithium aluminum hydride (1.4 g) in tetrahydrofuran (100 ml) is slowly dropped 6-chloro-2'-propionylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (6.1 g) in tetrahydrofuran (50 ml). The reaction mixture is heated under reflux for four hours, cooled and quenched by the dropwise addition of saturated ammonium chloride solution (100 ml). The mixture is filtered, diluted with ether, washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield an oil which is dissolved in ether and converted to the product hydrochloride salt (6.0 g, 90%). The salt is recrystallized from ethyl acetate/methanol to yield the analytical sample as a white solid, mp 227°-228° (dec.).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for four hours
  3. temperaturecooled
  4. customquenched by the dropwise addition of saturated ammonium chloride solution (100 ml)
  5. filtrationThe mixture is filtered
  6. additiondiluted with ether
  7. washwashed with water (2x), saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering
  10. customthe solvent is removed
  11. customto yield an oil which
  12. customThe salt is recrystallized from ethyl acetate/methanol
  13. customto yield the analytical sample as a white solid, mp 227°-228° (dec.)

Sources & evidence

ORD record
ord-0a13d4fc6c084d8cad3b98494c210328
Source dataset
uspto-grants-1983_02
Patent number
US04374137

Reaction notes

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