Dimethylformamide → HCID 22675509, compound

HRID 355763Notes

Reaction equation

HRID 355763 reaction equation
[CH2:1]([C:9]1[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=1[CH2:11][N:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)[CH2:13][CH3:14])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:28](Cl)(=O)[C:29](Cl)=O.[CH3:34][N:35](C=O)C>C(Cl)Cl>[CH2:34]([NH:35][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([N:12]([CH2:13][CH3:14])[CH2:11][C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]=2[CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:23][CH:22]=1)[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 22675498HCID 22675498, compound

Product 1

HCID 22675509HCID 22675509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[N-(2-(Phenethyl)benzyl)-N-ethylamino]benzoic acid (1.5 g), oxalyl chloride (0.43 ml), DMF (0.1 ml) and CH2Cl2 (50 ml) were stirred together for 2 hours. The solvent was evaporated and the residue re-dissolved in dichloromethane (100 ml). This was added to a solution of propylamine (0.35 ml) in dichloromethane (10 ml) at 0° C. The resulting mixture was stirred for 2 hours at ambient temperature, filtered and the filtrate purified by MPLC, eluting with ethyl acetate to give a gum. The gum was purified by crystallisation from diethyl ether/iso-hexane to give N-propyl-4-[N-ethyl-N-(2-(phenethyl)benzyl)-amino]benzamide e (0.31 g) as a white solid, (mpt. 91°/93° C.).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue re-dissolved in dichloromethane (100 ml)
  3. additionThis was added to a solution of propylamine (0.35 ml) in dichloromethane (10 ml) at 0° C
  4. filtrationfiltered
  5. customthe filtrate purified by MPLC
  6. washeluting with ethyl acetate
  7. customto give a gum
  8. customThe gum was purified by crystallisation from diethyl ether/iso-hexane

Sources & evidence

ORD record
ord-484d98f25c7542189090746e79646ff5
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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