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Formaldehyde → 9-(2-cyclohexylethyl)-2,3,4,9-tetrahydro-2,6-dimethyl-1H-pyrido[3,4-b]indole

HRID 1775909
Notes
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Reaction equation

HRID 1775909 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[C:11]([CH2:19][CH2:20][NH:21][CH3:22])=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23](O)(C(F)(F)F)=O.C=O>C(#N)C>[CH:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[C:11]3[CH2:19][CH2:20][N:21]([CH3:23])[CH2:22][C:10]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 669116442-(1-(2-cyclohexylethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine

Product 1

HCID 442421119-(2-cyclohexylethyl)-2,3,4,9-tetrahydro-2,6-dimethyl-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

The title compound was prepared by General Method 4. 2-(1-(2-cyclohexylethyl)-5-methyl-1H-indol-3-yl)-N-methylethanamine (72 mg) was dissolved in acetonitrile (2 mL) containing 5% TFA and the reaction mixture was heated to reflux. 37% aqueous formaldehyde (0.02 mL) was added and the reflux was continued for additional 2 h. The reaction mixture was cooled to 25° C., concentrated under reduced pressure and partitioned between ethyl acetate and satd. Aqueous NaHCO3. The organic layer was dried over sodium sulfate, evaporated under reduced pressure and the residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 9/1/0.1) to obtain 52 mg of product. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF. 1H NMR (DMSO) δ 7.5 (d, 1H), 7.4 (s, 1H), 6.9 (d, 1H), 4.3 (bs, 2H), 4.0 (t, 2H), 3.6 (bs, 2H), 2.8 (m, 5H), 2.3 (s, 3H), 1.8-0.7 (m, 13H). MS m/z observed 311. HPLC RT 5.93 min.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 9/1/0.1)

Sources & evidence

ORD record
ord-75d53614e38a44b58030d3c276a61099
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260429B2

Reaction notes

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