Sodium Sulfate → HCID 54152569, compound

HRID 2398292Notes

Reaction equation

HRID 2398292 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][C@@H:9]3[CH:12]=[CH:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[CH2:16][C@H:8]3[CH2:7]2)=O)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH:1]1([CH2:4][N:6]2[CH2:11][CH2:10][C@@H:9]3[CH:12]=[CH:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[CH2:16][C@H:8]3[CH2:7]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 54568333HCID 54568333, compound

Product 1

HCID 54152569HCID 54152569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.0 g of trans-2-cyclopropylcarbonyl-2,3,4,4a,11,11a-hexahydro-1H-benzo[5,6]cyclohepta[1,2-c]pyridine (obtained by reaction of trans-2,3,4,4a,11,11a-hexahydro-1H-benzo[5,6]cyclohepta[1,2-c]-pyridine with cyclopropanecarboxylic acid chloride) in 150 cc of anhydrous tetrahydrofuran is added dropwise, while stirring, at 10°-15°, to a solution of 2.5 g of lithium aluminium hydride in 350 cc of anhydrous tetrahydrofuran, and the reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is decomposed at 0°-5° by the dropwise addition of 12 cc of saturated sodium sulphate solution, the inorganic portion is filtered off and washed out with methylene chloride. The combined filtrates are dried over sodium sulphate, concentrated by evaporation, and the title compound obtained as oily residue is converted into the hydrogen fumarate in isopropanol/acetone and is recrystallized. M.P. 157°-159°.

Workup

  1. filtrationthe inorganic portion is filtered off
  2. washwashed out with methylene chloride
  3. dry with materialThe combined filtrates are dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3d22e560088446788c4e30908ed6004e
Source dataset
uspto-grants-1977_05
Patent number
US04024265

Reaction notes

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