Propylamine → HCID 19069300, compound

HRID 1781158Notes

Reaction equation

HRID 1781158 reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([NH2:20])[CH2:18][CH3:19].CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:17]([NH:20][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:16][CH:15]=1)[CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8857Ethyl AcetateHCID 2923314-(Phenylamino)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 19069300HCID 19069300, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.06 g (5.0 mmol, 1 eq.) of 4-phenylaminobenzoic acid, prepared by the method of Portnaya, et al., Zhur. Obshchei. Khim., 30: 2693 (1960), n-propylamine (0.82 mL, 10.0 mmol, 2 eq.) and 0.061 g (0.5 mmol, 0.1 eq.) of DMAP in THF at 0° C. was added 1.05 g (5.5 mmol, 1.1 eq.) of EDCl. The mixture was stirred overnight while the bath melted. The mixture was poured into 150 mL of ethyl acetate and extracted with 50 mL each of water, 1N aqueous HCl, water, and saturated aqueous NaHCO3 solution. The ethyl acetate layer was then dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on SiO2 eluting with 1:1 ethyl acetate-hexanes to give 0.51 g (40%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 10.57 (bs, 2H), 7.21-7.41 (m, 9H), 3.96 (s, 2H), 2.75 (m, 2H), 1.64 (hextet, 2H), 0.92 (t, 3H). MS (DCl) m/e 255 (M+H)+.

Workup

  1. extractionextracted with 50 mL each of water, 1N aqueous HCl, water, and saturated aqueous NaHCO3 solution
  2. dry with materialThe ethyl acetate layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on SiO2 eluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-d9b649ba151849c18f73f4aaffbe6ca0
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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