Pentylamine → Methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoate

HRID 330178Notes

Reaction equation

HRID 330178 reaction equation
[C:1]([CH:4]([CH3:29])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[CH:10]=[C:9]2[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=1[O:27][CH3:28])(O)=[O:2].Cl.CN(C)CCCN=C=NCC.[CH2:42]([NH2:47])[CH2:43][CH2:44][CH2:45][CH3:46]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:28][O:27][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][C:17]=1[CH2:16][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][CH:4]([C:1](=[O:2])[NH:47][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH3:29])[CH:7]=2)[N:11]([CH3:15])[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 8060PentylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14882558Methyl 4-[5-(2-carboxypropyl)-1-methylindol-3-ylmethyl]-3-methoxybenzoate

Product 1

HCID 14882559Methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoateYield 80.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methyl 4-[5-(2-carboxypropyl)-1-methylindol-3-ylmethyl]-3-methoxybenzoate (0.7 g), 4-dimethylaminopyridine (0.249 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.391 g) and pentylamine (0.154 g) was dissolved in methylene chloride (15 ml), and stirred for 18 hr, under an atmosphere of nitrogen. Methylene chloride (50 ml) was added, the solution was washed with 1M hydrochloric acid and brine, and dried (MgSO4). The solvent was evaporated and the residual oil purified by flash chromatography, eluting with 40:50:5 hexane:methylene chloride:ethyl acetate, to give a foam which was crystallized from a mixture of methylene chloride and hexane to give methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoate (0.66 g, 80%) as white crystals; mp 128°-130°; partial NMR (250 MHz, DMSO-d6): 0.78(t, J=7 Hz, 3H, CH2CH3), 0.95(d, J=6.4 Hz, 3H, CHCH3), 1.05-1.25[m, 6H, (CH2)3 ], 2.5(m, 2H), 2.9(m, 3H), 3.68(s, 3H), 3.83(s, 3H), 3.92(s, 3H), 3.99(s, 2H, ArCH2Ar'), 7.61(br t, 1H, NHCO).

Workup

  1. washthe solution was washed with 1M hydrochloric acid and brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe residual oil purified by flash chromatography
  5. washeluting with 40:50:5 hexane
  6. custommethylene chloride:ethyl acetate, to give a foam which
  7. customwas crystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-0e26ce4617914dfc860def0c1489deb3
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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