Hydrochloric Acid → Methyl 4-(5-hexanamido-1-methylindol-3-ylmethyl)-3-methoxybenzoate

HRID 275121Notes

Reaction equation

HRID 275121 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[C:13]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32].CN1CCOCC1.Cl>ClCCl>[C:1]([NH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[CH:14]=[C:13]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 67340Hexanoyl chlorideHCID 11209537Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Product 1

HCID 23365856Methyl 4-(5-hexanamido-1-methylindol-3-ylmethyl)-3-methoxybenzoateYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hexanoylchloride (0.029 g.) was added to a stirred solution of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (D) (0.05 g.) and N-methylmorpholine (0.05 g.) in dichloromethane (3 ml.), under an atmosphere of nitrogen. The mixture was stirred for 2 hours and then poured into 1M hydrochloric acid (15 ml.). This mixture was extracted with ethyl acetate (2×20 ml.). The combined extracts were dried (MgSO4), and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 4:6 v/v ethyl acetate:hexane, to give a colorless oil, which was crystallized from a mixture of toluene and hexane to give the title compound (0.05 g, 65%) as a white powder; NMR: 0.86(t, 3H, CH2.CH3), 1.28(m,4H, CH2.CH2.CH3), 1.57(quintet, 2H, CH2.CH2.CON), 2.25(t,2H, CH2.CH2.CON), 3.69(s,3H, NCH3), 3.82(s,3H, CO.OCH3), 3.92(s,3H, OCH3), 3.97(s, 2H, CH2.Ar), 7.05 (s,1H), 7.13(d,1H), 7.27(d,1H), 7.28(d,1H), 7.40(dd,1H), 7.48(s,1H), 7.74(s,1H), 9.61(s,1H).

Workup

  1. extractionThis mixture was extracted with ethyl acetate (2×20 ml.)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customThe residual oil was purified by flash chromatography on silica gel (50 ml.)
  5. washeluting with 4:6 v/v ethyl acetate
  6. customhexane, to give a colorless oil, which
  7. customwas crystallized from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-6fb1079ee960426d9b5ee57950cff001
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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