Phenethylamine → HCID 21217929, compound

HRID 1586216Notes

Reaction equation

HRID 1586216 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH2:12][C:13]([OH:15])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:24]([NH2:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH2:12][C:13]([NH:32][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:15])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10709631HCID 10709631, compound

Product 1

HCID 21217929HCID 21217929, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Part A. 4-(cyano)-beta-[3-(cyano)phenyl]benzene pentanoic acid (0.150 gm, 0.49 mmol) was dissolved in dry DMF and phenethyl amine (0.065 gm, 0.54 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.140 gm, 0.74 mmol) and 4-dimethylaminopyridine (0.150 gm, 1.2 mmol) were added. The resulting solution was stirred at room temperature for 48 hrs., quenched in 1 N HCl and extracted with ethyl acetate. The organic phase was washed with 1 N HCl, water and brine and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica gel eluting ethyl acetate:toluene(30:70, v:v) to give 4-(cyano)-beta-[3-(cyano)phenyl]-N-(2-phenylethyl)benzenepentanamide as an oil 0.100 gm (50%). MS: (M+H)+ 408; 1H NMR (CDCl3): 1.9 (m,1H), 2.35 (dd, 1H), 2.45 (m, 2H), 2.7(m, 3H), 3.25(m, 1H), 3.45 (m, 3H), 7.0 (d, 2H), 7.2 (m, 6H), 7.45 (m, 3H), 7.55 (m, 3H).

Workup

  1. custom, quenched in 1 N HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 1 N HCl, water and brine
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. customthe residue was chromatographed on silica gel
  7. washeluting ethyl acetate:toluene(30:70, v:v)

Sources & evidence

ORD record
ord-8892ef8f95b04f76bf4003cacd12a869
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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