Methylamine → HCID 67996289, compound

HRID 659617Notes

Reaction equation

HRID 659617 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH:19]([C:23](OCC)=[O:24])[CH2:18]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].ClCCl.CO.[CH3:33][NH2:34]>[O-]S([O-])(=O)=O.[Cu+2]>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH:19]([C:23]([NH:34][CH3:33])=[O:24])[CH2:18]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 28384153-Piperidinecarboxylic acid, 1-[(9-ethyl-9H-carbazol-3-yl)methyl]-, ethyl esterHCID 21226129Dichloromethane methanol

Product 1

HCID 67996289HCID 67996289, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Conditions

Temperature
140 °C

Procedure

A 50-mL seal tube charge with a solution of ethyl 1-((9-ethyl-9H-carbazol-3-yl)methyl)piperidine-3-carboxylate (500 mg, 1.37 mmol, 1.00 equiv) in CH3NH2 (25 mL). To the mixture was added CuSO4 (100 mg, 0.51 mmol, 0.37 equiv). The resulting solution was stirred at 140° C. for 24 hours in an oil bath. The progress was monitored by TLC (dichloromethane/methanol=5:1). Upon completion, the solids were filtered out. The resulting solution was extracted with dichloromethane (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography eluted with dichloromethane/methanol (30:1) affording 1-((9-ethyl-9H-carbazol-3-yl)methyl)-N-methylpiperidine-3-carboxamide as white solid (28 mg, 6%). LCMS: [M+H]+: 350. 1H NMR (CDCl3, 300 MHz) δ 8.10 (d, 1H), 8.01 (s, 1H), 7.53-7.39 (m, 4H), 7.29-7.24 (m, 1H), 4.44-4.37 (q, 2H), 3.85-3.81 (d, 1H), 3.69-3.65 (d, 1H), 2.89 (m, 2H), 2.80-2.78 (d, 3H), 2.59 (br, 1H), 2.45 (br, 2H), 1.91 (m, 1H), 1.73-1.73 (m, 3H), 1.47 (t, 3H).

Workup

  1. customA 50-mL seal tube
  2. filtrationUpon completion, the solids were filtered out
  3. extractionThe resulting solution was extracted with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with dichloromethane/methanol (30:1)

Sources & evidence

ORD record
ord-d5c8c682f77d46c0b06a155d142909cb
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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