Hydrochloric Acid → Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate

HRID 1904467Notes

Reaction equation

HRID 1904467 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25].[CH:26]1([CH2:31][C:32](O)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:26]1([CH2:31][C:32]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]3[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 71606Cyclopentylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23365902HCID 23365902, compound

Product 1

HCID 14626833Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoateYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the ester (H) described above (used without further characterization) (4.43 g), cyclopentylacetic acid (1.85 g), 4-(dimethylamino)pyridine (1.76 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.26 g), was dissolved in methylene chloride (100 ml), under an atmosphere of nitrogen, and stirred at room temperature for 18 hours. The mixture was poured into 1M hydrochloric acid (25 ml), the separated aqueous layer extracted with dichloromethane (2×100 ml), the combined organic extracts washed with water, brine, dried (MgSO4) and evaporated. The residual oil was crystallized from ethanol to give off-white needles which were recrystallized from methylene chloride/hexane to give methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate (I) as a white powder (5.12 g, 87%); mp 144°-146° C.; partial NMR (250 MHz, DMSO-d6): 1.17(m, 2H), 1.32(t, 3H), 1.4-1.8(m, 6H), 2.25(m, 3H), 3.82(s, 3H, OCH3), 3.92(s, 3H, OCH3), 3.97 (s, 2H, ArCH2), 4.09(q, 2H, CH2CH3), 9.61(s, 1H, NH).

Workup

  1. extractionthe separated aqueous layer extracted with dichloromethane (2×100 ml)
  2. washthe combined organic extracts washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual oil was crystallized from ethanol
  6. customto give off-white needles which
  7. customwere recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-6d15baa4e911421483a426202ee775ae
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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