HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethanol → 2-(1-(2-cyclohexylethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine

HRID 2198289
Notes
Print preview

Reaction equation

HRID 2198289 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)N)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCO.C(O[CH:24](OCC)[CH2:25][CH2:26][CH2:27][NH:28][CH3:29])C>O.Cl>[CH:1]1([CH2:7][CH2:8][N:9]2[C:11]3[C:16](=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[C:25]([CH2:26][CH2:27][NH:28][CH3:29])=[CH:24]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 702EthanolHCID 139945474,4-Diethoxy-N-methylbutan-1-amineHCID 669116431-(2-Cyclohexylethyl)-1-p-tolylhydrazine

Product 1

HCID 669116442-(1-(2-cyclohexylethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×
HCID 962
Water
Solvent

Conditions

Temperature
90 °C

Procedure

The title compound was prepared by General Method 3. A solution of 1-(2-cyclohexylethyl)-1-p-tolylhydrazine (0.15 g) in water (1 mL) and conc. HCl (0.18 mL) was heated to 60° C. EtOH (1 mL) was added followed by 4,4-diethoxy-N-methylbutan-1-amine (0.12 g) and the temperature was raised to 90° C. Conc. HCl (0.1 mL) was added and the heating was continued for an additional 6 h after which the reaction mixture was cooled and stirred at 25° C. for 12 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 9/1/0.1) to obtain 79 mg of product.

Workup

  1. temperatureafter which the reaction mixture was cooled
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 9/1/0.1)

Sources & evidence

ORD record
ord-70c58b44710f4c489f20e4dc7bc181bf
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08338447B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes