2-(4-Methoxyphenoxy)ethylamine → Alpha-isopropyl-alpha-[3-[N-[2-(4-methoxyphenoxy)ethyl]amino]-propyl]-3,4-dimethoxyphenylacetonitrile

HRID 65090Notes

Reaction equation

HRID 65090 reaction equation
[C:1]([C:3]([CH:18]([CH3:20])[CH3:19])([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[CH2:4][CH2:5][CH:6]=O)#[N:2].[CH3:21][O:22][C:23]1[CH:32]=[CH:31][C:26]([O:27][CH2:28][CH2:29][NH2:30])=[CH:25][CH:24]=1.[BH4-].[Na+]>C(O)C>[CH:18]([C:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)([CH2:4][CH2:5][CH2:6][NH:30][CH2:29][CH2:28][O:27][C:26]1[CH:31]=[CH:32][C:23]([O:22][CH3:21])=[CH:24][CH:25]=1)[C:1]#[N:2])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 17977932-(4-Methoxyphenoxy)ethylamineHCID 30153703-(3,4-Dimethoxyphenyl)-2-methyl-6-oxohexane-3-carbonitrileHCID 4311764Sodium borohydride

Product 1

HCID 13714713Alpha-isopropyl-alpha-[3-[N-[2-(4-methoxyphenoxy)ethyl]amino]-propyl]-3,4-dimethoxyphenylacetonitrileYield 57.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.96 g of 4-cyano-4-isopropyl-4-(3,4-dimethoxyphenyl)butyraldehyde and 2.00 g of 2-(4-methoxyphenoxy)ethylamine in 50 ml of ethanol was refluxed for 1 hour. To the solution was added 0.55 g of sodium borohydride under ice-cooling, and the solution was stirred for 30 minutes at room temperature. The solvent was removed and the residue was dissolved in 10% hydrochloric acid and washed with ether. The aqueous layer was made alkaline with potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue was chromatographed on silica gel using chloroform as an eluent to give 2.93 g of the desired compound as a pale yellow oil.

Workup

  1. temperaturecooling
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in 10% hydrochloric acid
  4. washwashed with ether
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-8c07906cda044c0d91383a292b90ea13
Source dataset
uspto-grants-1986_09
Patent number
US04612329

Reaction notes

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