Hydrochloric Acid → Methyl 4-(5-hexanamidoindol-3-ylmethyl)-3-methoxybenzoate

HRID 275115Notes

Reaction equation

HRID 275115 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23].CN1CCOCC1.[C:31](Cl)(=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].Cl>ClCCl>[C:31]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23])(=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 67340Hexanoyl chlorideHCID 23365920Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365832Methyl 4-(5-hexanamidoindol-3-ylmethyl)-3-methoxybenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate (A) (0.2 g.) in dichloromethane (5 ml. ) under an atmosphere of nitrogen, was treated with N-methylmorpholine (0.25 g.), followed by hexanoyl chloride (0.103 g.). After being stirred for 2 hours, the mixture was poured into 1M hydrochloric acid (20 ml.). This mixture was extracted with ethyl acetate (2×20 ml.). The combined organic extracts were dried (MgSO4) and evaporated. The yellow oil obtained was purified by flash chromatography on silica gel (75 ml.), eluting with 6:4 v/v ethyl acetate:hexane, to give the title compound (0.24 g., 92%) as a colorless oil; NMR: 0.83(t,3H, CH2.CH3), 1.36(m,4H, CH2.CH2.CH3), 1.57(quintet,2H, CH2.CH2.CON), 2.24(t, 2H, CH2.CON), 3.80(s,3H, COOCH3), 3.90(s,3H, OCH3), 3.99(s,2H, CH2. Ar), 7.1(m, 2H), 7.21(m,2H), 7.44(m,2H), 7.69(s,1H, H4 -indole), 9.59(s,1H, CONH), 10.77(s,1H, H1 -indole).

Workup

  1. extractionThis mixture was extracted with ethyl acetate (2×20 ml.)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customevaporated
  4. customThe yellow oil obtained
  5. customwas purified by flash chromatography on silica gel (75 ml.)
  6. washeluting with 6:4 v/v ethyl acetate

Sources & evidence

ORD record
ord-eb4fb57c81634561818f794e41af7fd8
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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