Triethylamine → ethyl 5,6-dihydro-11-chloro-4H-azocino[3,2,1-hi]indole-2-carboxylate

HRID 650074Notes

Reaction equation

HRID 650074 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 21714297ethyl 5,6,7,8-tetrahydro-11-chloro-8-hydroxy-4H-azocino [3,2,1-hi]indole-2-carboxylate

Product 1

HCID 70238243ethyl 5,6-dihydro-11-chloro-4H-azocino[3,2,1-hi]indole-2-carboxylateYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of ethyl 5,6,7,8-tetrahydro-11-chloro-8-hydroxy-4H-azocino[3,2,1-hi]indole-2-carboxylate (0.70 g, 2.27 mmol), triethylamine (0.61 g, 6.00 mmol) and tetrahydrofuran (30 ml) was cooled to −20° C. with stirring, and methanesulfonyl chloride (0.31 g, 2.73 mmol) was added dropwise. After completion of the dropwise addition, the reaction temperature was raised to room temperature and the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was poured into an aqueous ammonium chloride solution and extracted twice with ethyl acetate, and the extract solution was washed with an aqueous sodium hydrogencarbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain 0.63 g of ethyl 5,6-dihydro-11-chloro-4H-azocino[3,2,1-hi]indole-2-carboxylate.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe reaction temperature was raised to room temperature
  3. extractionextracted twice with ethyl acetate
  4. washthe extract solution was washed with an aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

Sources & evidence

ORD record
ord-90001a8b349b4265b41dad35c42627ba
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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