2,3-Dihydroxybutanedioic Acid → 2-[3-[(Phenylethyl)methylamino]-propyl]-2-isopropylphenylacetaldehyde

HRID 3989

Reaction equation

HRID 3989 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([CH2:17][CH2:18][N:19]([CH3:35])[CH2:20][CH2:21][CH2:22][C:23]([CH:32]([CH3:34])[CH3:33])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:24]#N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)[OH:37].C(O)(=O)C(C(C(O)=O)O)O.[OH-].[K+]>CCCCCC.C(OCC)C>[C:11]1([CH2:17][CH2:18][N:19]([CH3:35])[CH2:20][CH2:21][CH2:22][C:23]2([CH:32]([CH3:34])[CH3:33])[CH:24]=[CH:29][CH:30]=[CH:31][CH:26]2[CH2:27][CH:28]=[O:37])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 712255-[Methyl(2-phenylethyl)amino]-2-phenyl-2-propan-2-ylpentanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 886380192-[3-[(Phenylethyl)methylamino]-propyl]-2-isopropylphenylacetaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

180 ml of a 1M solution of diisobutylaluminum hydride in hexane were added dropwise, at -5° C., to a solution of 33.4 g (0.1 mole) of 2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile in 400 ml of diethyl ether. The mixture was stirred for 1.5 hours, after which 500 ml of 10% strength sulfuric acid were added. 30 g of tartaric acid were introduced, the mixture was rendered alkaline with concentrated potassium hydroxide solution, and the ether phase was separated off and washed several times with sodium chloride solution. After the ether phase had been dried over sodium sulfate, the ether was distilled off, the remaining oily residue was dissolved in 300 ml of ethyl acetate, and hydrochloric acid in isopropanol was added. The mixture was left to stand overnight, after which the precipitated hydrochloride was filtered off under suction.

Workup

  1. customthe ether phase was separated off
  2. washwashed several times with sodium chloride solution
  3. dry with materialAfter the ether phase had been dried over sodium sulfate
  4. distillationthe ether was distilled off
  5. dissolutionthe remaining oily residue was dissolved in 300 ml of ethyl acetate
  6. additionhydrochloric acid in isopropanol was added
  7. waitThe mixture was left
  8. waitto stand overnight
  9. filtrationafter which the precipitated hydrochloride was filtered off under suction

Sources & evidence

ORD record
ord-9e27edb996dc4b2e8698c669aeab451a
Source dataset
uspto-grants-1988_02
Patent number
US04723039

Linked notes

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