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

Sodium Bicarbonate → 2,3,4,5-tetrahydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole

HRID 509701
Notes
Print preview

Reaction equation

HRID 509701 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]3[CH2:19][CH2:20][N:21](C(OCC(Cl)(Cl)Cl)=O)[CH2:22][C:5]=3[C:4]=2[CH:3]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.[Zn]>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]3[CH2:19][CH2:20][NH:21][CH2:22][C:5]=3[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 578759012,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 578763102,3,4,5-tetrahydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indoleYield 51.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic Acid
Solvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,2,2-trichloroethyl 3,4-dihydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (100 mg, 0.2 mmol) and Zn dust (120 mg, 1.9 mmol) in acetic acid (1.2 ml) was stirred at 25° C. for 2 h. The reaction mixture was basified with saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated to obtain 30 mg of 2,3,4,5-tetrahydro-8-methyl-5-phenethyl-1H-pyrido[4,3-b]indole after purification on silica gel (230-400 mesh) chromatography eluting with methanol-dichloromethane gradient.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-6a32fe047bc84b8ba38eb4472d349eee
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096591B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes