Triethylamine → HCID 46222161, compound

HRID 1641038Notes

Reaction equation

HRID 1641038 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].C(N(CC)CC)C.[CH2:26]([CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][NH2:38])[CH2:32][CH2:31]1)[CH2:27][CH2:28][CH3:29]>C(OCC)C.ClCCl>[CH2:26]([CH:30]1[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][NH:38][C:13](=[O:17])[C:14]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[O:15])[CH2:34][CH2:35]1)[CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 65578Oxalyl chlorideHCID 4389257HCID 4389257, compoundHCID 22989601HCID 22989601, compound

Product 1

HCID 46222161HCID 46222161, compoundYield 2.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-isopropyl indole (100 mg, 0.63 mmol) in diethyl ether (2 mL) at 0° C. was drop-wise added oxalyl chloride (60 mL, 0.73 mmol). The mixture was allowed to warm to room temperature over a period of three hours and then concentrated in vacuo to give a yellow solid. To the yellow solid was added dichloromethane (2 mL), triethyl amine (0.525 mL, 3.77 mmol), and a solution of the crude 2-(4-butylpiperidin-1-yl)ethanamine (150 mg) in triethyl amine (0.525 mL, 3.77 mmol) and dichloromethane (1 mL). The mixture was stirred at room temperature for 66 hours, then washed with saturated aqueous sodium bicarbonate (1×5 mL) and water (1×5 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give a yellow oil, which was purified by silica chromatography on a Biotage (2-10% MeOH/CH2Cl2) to give a yellow gum (6 mg, 2% yield): 1H NMR (400 MHz, CDCl3): δ 9.11 (s, 1H), 8.46 (m, 1H), 7.92 (t, 1H), 7.43 (m, 1H), 7.33 (m, 2H) 4.71 (m, 1H), 3.47 (q, 2H), 2.45 (d, 2H), 2.54 (t, 2H), 1.98 (t, 2H), 1.65 (m, 2H), 1.61 (d, 6H), 1.25 (m, 9H), 0.89 (t, 3H); MS (ESI) m/z: Calculated for C24H35N3O2: 397.3. Found: 398.3 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a yellow solid
  3. washwashed with saturated aqueous sodium bicarbonate (1×5 mL) and water (1×5 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil, which
  8. customwas purified by silica chromatography on a Biotage (2-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-392dec97dab8419d94b63b03257adc3d
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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