Propylamine → HCID 19069300, compound

HRID 1957338Notes

Reaction equation

HRID 1957338 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>[C:1]1([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:20][CH2:17][CH2:18][CH3:19])=[O:14])=[CH:15][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

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 (Portnaya, B. S., Turitsyna, N. F., Bobkova, T. P., and Levkeov, I. I., 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 washed with 50 mL each of water, 1N aqueous HCl, water and saturated aqueous NaHCO3. The ethyl acetate layer was then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (80 g SiO2, 1:1 ethyl acetate-hexanes) to give 0.51 g (40%) of the title compound. 1H NMR (300 MHz, CDCl3) δ10.57 (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. washwashed with 50 mL each of water, 1N aqueous HCl, water and saturated aqueous NaHCO3
  2. dry with materialThe ethyl acetate layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (80 g SiO2, 1:1 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-26096e70c2c94761b9c9309d6ec8f58f
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

Loading…