Sulfuric Acid → HCID 57875974, compound

HRID 1465284Notes

Reaction equation

HRID 1465284 reaction equation
Cl.[CH3:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)N)=[CH:5][CH:4]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=O.S(=O)(=O)(O)O>O1CCOCC1>[CH3:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[C:13]3[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=3[C:25]3[CH2:24][NH:23][CH2:28][CH2:27][C:26]2=3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 126652-PiperidoneHCID 68735622HCID 68735622, compound

Product 1

HCID 57875974HCID 57875974, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate-hydrochloride (0.15 gm, 0.447 mol), piperidone (0.13 gm, 1.34 mol) and 7% sulfuric acid in dioxane (5 mL) was heated at 100 deg C. for 2 h. Reaction mass was cooled and concentrated under reduced pressure to give crude 2,3,4,5-tetrahydro-5-(2-(6-methylpyridin-3-yl)ethyl)-1H-pyrido[4,3-b]indole-8-carboxylic acid (LCMS; 44% of desired peak) as a brown colored oil which is submitted for purification by preparative HPLC.

Workup

  1. temperaturewas heated at 100 deg C
  2. customReaction mass
  3. temperaturewas cooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c095bef24f248ff89a77dd8d4806f3a
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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