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

HRID 1646330Notes

Reaction equation

HRID 1646330 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 (2x20 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,3 H, CH2.CH3), 1.36 (m,4 H, CH2.CH2.CH3), 1.57 (quintet,2 H, CH2.CH2CON), 2.24 (t, 2 H, CH2.CON), 3.80 (s,3 H, COOCH3), 3.90 (s,3 H, OCH3), 3.99 (s,2 H, CH2.Ar), 7.1 (m, 2 H), 7.21 (m,2 H), 7.44 (m,2 H), 7.69 (s,1 H,H4 -indole), 9.59 (s,1 H, CONH), 10.77 (s,1 H, H1 -indole).

Workup

  1. extractionThis mixture was extracted with ethyl acetate (2x20 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-8add2c1f6b124d3c9c1439193a9aa3c6
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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