Triethylamine → HCID 44771633, compound

HRID 873671Notes

Reaction equation

HRID 873671 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](Cl)=[O:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:14][C:15]([CH3:20])([CH3:19])[C:16]([N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:1]1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 107838Tetrahydro-beta-carboline

Product 1

HCID 44771633HCID 44771633, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (2 g, 11.6 mmol) dissolved in methylene chloride (20 mL) is added 2,2-dimethyl-propionyl chloride (1.42 mL, 11.6 mmol) followed by the addition of triethylamine (1.61 mL, 11.6 mmol). The reaction mixture is stirred at room temperature for 30 minutes. The reaction is quenched with water and extracted with methylene chloride three times. The combined organic extracts are washed with saturated sodium bicarbonate, a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo to give 2.8 g (94%) of the title compound as a grey solid.

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted with methylene chloride three times
  3. washThe combined organic extracts are washed with saturated sodium bicarbonate
  4. dry with materiala saturated sodium chloride solution, dried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-386dceed37f24747b7b85773f7faf408
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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