Hydrochloric Acid → HCID 19921693, compound

HRID 1647796Notes

Reaction equation

HRID 1647796 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=O)[CH:12]=2)[NH:7][CH:6]=1.C(N(CC)CC)C.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].[Cl:33][C:34]1C=CC=C[N+]=1C.[ClH:41]>C(#N)C>[CH2:34]([Cl:33])[Cl:41].[CH3:2][OH:1].[NH4+:7].[OH-:1].[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH:31][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:16])[CH:12]=2)[NH:7][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19921669HCID 19921669, compound

Product 2

HCID 19921693HCID 19921693, compoundYield 37%HCID 21896990Dichloromethane methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(3-hydroxypropyl)-1H-indole-5-carboxylic acid (4.30 g, 19.63 mmol), triethylamine (3.97 g, 39.26 mmol) and benzylamine (2.10 g, 19.63 mmol) in 150 mL acetonitrile was added 2-chloro-1-methylpyridinium iodide (6.04 g, 23.68 mmol). The mixture was heated to reflux for 16 h. The solution was cooled to room temperature, 70 mL of 0.5N hydrochloric acid added, and the acetonitrile removed in vacuo. The residue was extracted with 250 mL of ethyl acetate. The organic layer was separated and the aqueous layer reextracted with three 50 mL portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (95:5:0.5 CH2Cl2 -MeOH-NH4OH) of the concentrate yielded 3-(3-hydroxypropyl)-N-(phenylmethyl)-1H-indole-5-carboxamide (2.26 g, 37%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 h
  3. customthe acetonitrile removed in vacuo
  4. extractionThe residue was extracted with 250 mL of ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf5f3dbb716a4511a5d9f8d1eb130157
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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