Triethylamine → N-isopropyl-6-phenoxycarbonylamino-1,2,3,4-tetrahydrocarbazole

HRID 50618Notes

Reaction equation

HRID 50618 reaction equation
[CH:1]([N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([NH2:17])[CH:9]=2)([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>ClCCl>[CH:1]([N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([NH:17][C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27])[CH:9]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 12992579N-isopropyl-6-amino-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 22736147N-isopropyl-6-phenoxycarbonylamino-1,2,3,4-tetrahydrocarbazoleYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N-isopropyl-6-amino-1,2,3,4-tetrahydrocarbazole (9.84 g) and 5.05 g of triethylamine were dissolved in 100 mL of dichloromethane, and added dropwise with 7.85 g of phenyl chloroformate. The reaction mixture was stirred at room temperature for 3 hours, then washed with 10% aqueous citric acid and then with saturated aqueous sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=8/2) and recrystallized from a mixture of hexane and ethyl acetate, to obtain 2.27 g of N-isopropyl-6-phenoxycarbonylamino-1,2,3,4-tetrahydrocarbazole.

Workup

  1. washwashed with 10% aqueous citric acid
  2. dry with materialwith saturated aqueous sodium hydrogencarbonate, and dried over anhydrous sodium sulfate
  3. customAfter the solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=8/2)
  5. customrecrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-38f8ccac7ecc46768baf854bdb1c427c
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Reaction notes

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