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

HRID 1756360Notes

Reaction equation

HRID 1756360 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-06b56fce93534f908769633f1319484f
Source dataset
uspto-grants-1995_08
Patent number
US05440035

Reaction notes

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