Triethylamine → HCID 18974075, compound

HRID 2395040Notes

Reaction equation

HRID 2395040 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][CH2:9][CH2:10][C:11]([OH:13])=O.Cl.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:11](=[O:13])[CH2:10][CH2:9][O:8][CH3:7])=[CH:34][CH:33]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1344423-Methoxypropionic acidHCID 18973995HCID 18973995, compound

Product 1

HCID 18974075HCID 18974075, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.41 ml) was added to a stirred solution of 3-methoxypropanoic acid (0.45 ml) in methylene chloride (15 ml) containing 1 drop of N,N-dimethylformamide. The mixture was stirred at ambient temperature for 3 hours. A 5 ml aliquot of this reaction mixture was added dropwise to a solution of 4-[3-(2-benzyloxyphenyl)-propyl]-benzeneamine hydrochloride (0.63 g) in dichloromethane (20 ml) containing triethylamine (0.82 ml). Stirring was containued for 16 hours. The reaction mixture was evaporated to dryness and the residue was partitioned between diethyl ether and water. The diethyl ether extract was washed consecutively with aqueous 2N HCl (20 ml), saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml) then dried (MgSO4). The residue obtained on removal of the solvent was subjected to flash chromatography on silica (Merck 9385) eluted with ether, to give, after crystallisation from diethyl ether-hexane mixture, 4-[3-(2-benzyloxyphenyl)propyl]-N-(3-methoxypropionyl)-benzeneamine, m.p. 65°-6° C., yield 0.58 g (80%).

Workup

  1. stirringStirring
  2. waitwas containued for 16 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue was partitioned between diethyl ether and water
  5. extractionThe diethyl ether extract
  6. washwas washed consecutively with aqueous 2N HCl (20 ml), saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml)
  7. dry with materialthen dried (MgSO4)
  8. customThe residue obtained on removal of the solvent
  9. washeluted with ether
  10. customto give
  11. customafter crystallisation from diethyl ether-hexane mixture, 4-[3-(2-benzyloxyphenyl)propyl]-N-(3-methoxypropionyl)-benzeneamine, m.p. 65°-6° C., yield 0.58 g (80%)

Sources & evidence

ORD record
ord-0c1f9652d4c74cffb452101dc852ec47
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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