Hydrochloric Acid → Methyl 4-(1-benzyl-5-hexanamidoindol-3-ylmethyl)-3methoxybenzoate

HRID 1646339Notes

Reaction equation

HRID 1646339 reaction equation
CC(C)([O-])C.[K+].[C:7]([NH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=1[O:35][CH3:36])(=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl>O1CCCC1>[CH2:37]([N:20]1[C:21]2[C:17](=[CH:16][C:15]([NH:14][C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:23][CH:22]=2)[C:18]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=2[O:35][CH3:36])=[CH:19]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 23365832Methyl 4-(5-hexanamidoindol-3-ylmethyl)-3-methoxybenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 57133624Methyl 4-(1-benzyl-5-hexanamidoindol-3-ylmethyl)-3methoxybenzoateYield 22.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (0.04 g.) was added to a stirred solution of methyl 4-(5-hexanamidoindol-3-ylmethyl)-3-methoxybenzoate (0.15 g.) in dry tetrahydrofuran (5 ml.), under an atmosphere of nitrogen. The resulting dark-green mixture was stirred for 30 minutes. Benzyl bromide (0.062 g.) was added, causing the color to change to light brown. After 1 hour, the mixture was poured into 1M hydrochloric acid (20 ml.). This mixture was extracted with ethyl acetate (2×25 ml.). The combined extracts were dried (MgSO4) and evaporated. The brown oil obtained was purified by flash chromatography on silica gel (50 ml.), eluting with 3:7 v/v ethyl acetate:hexane, to give the title compound (0.04 g, 17%) as an oil; NMR: 0.86 (t,3 H, CH2.CH3), 1.27 (m,4 H, CH2.CH2.CH3), 1.57 (m,2 H, CH2.CH2.CON), 2.24 (t,2 H, CH2.CH 2.CON), 3.82 (s,3 H, CO.OCH3), 3.91 (s,3 H, OCH3), 3.99 (s,2 H, CH2.Ar), 5.32 (s,2 H, NCH2Ph), 7.21 (m,10 H), 7.44 (m,2 H), 7.75 (d, 1 H), 9.64 (s,1 H, NH).

Workup

  1. waitAfter 1 hour
  2. extractionThis mixture was extracted with ethyl acetate (2×25 ml.)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated
  5. customThe brown oil obtained
  6. customwas purified by flash chromatography on silica gel (50 ml.)
  7. washeluting with 3:7 v/v ethyl acetate

Sources & evidence

ORD record
ord-ea421f70e726444e844c6fd16b9ddbe4
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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