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

HRID 2195847Notes

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

Participants

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

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-6b13b5fa1cbe409fabb1d32b6d2d18e4
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338408B2

Reaction notes

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