Triethylamine → HCID 118717935, compound

HRID 968639Notes

Reaction equation

HRID 968639 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18](Cl)(=[O:22])C([Cl:21])=O.C(N(CC)CC)C.[CH2:31]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH3:32]>ClC(Cl)C(Cl)Cl>[ClH:21].[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=3)[C:10]([C:18]([N:36]3[CH2:37][CH2:38][N:33]([CH2:31][CH3:32])[CH2:34][CH2:35]3)=[O:22])=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 791961-EthylpiperazineHCID 63851488HCID 63851488, compound

Product 1

HCID 118717935HCID 118717935, compound

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

To a solution of 1-(cyclohexylmethyl)-5-fluoroindole (208 mg, 0.9 mmol) in 1,1,2,2-tetrachloroethane (15 ml) at 0° C., was added oxalyl chloride (0.122 ml, 0.945 mmol) with stirring under a stream of nitrogen. The mixture was allowed to warm to room temperature over 1 hour, then heated to 120° C. for a further 1.5 hours. The mixture was cooled to room temperature and triethylamine (0.138 ml, 0.99 mmol) was added. Stirring was continued for a further 10 minutes before the addition of N-ethylpiperazine (0.125 ml, 0.99 mmol). The mixture was stirred at room temperature for 15 hours and then partitioned between 0.4 M sodium hydroxide solution (10 ml) and dichloromethane (10 ml). The organic layer was washed with water (10 ml), dried over Na2SO4 and concentrated. The resulting brown oil was purified by flash chromatography using 95% dichloromethane, 5% methanol as eluent to yield the title compound as the free base.

Workup

  1. temperatureheated to 120° C. for a further 1.5 hours
  2. temperatureThe mixture was cooled to room temperature
  3. stirringStirring
  4. stirringThe mixture was stirred at room temperature for 15 hours
  5. custompartitioned between 0.4 M sodium hydroxide solution (10 ml) and dichloromethane (10 ml)
  6. washThe organic layer was washed with water (10 ml)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe resulting brown oil was purified by flash chromatography

Sources & evidence

ORD record
ord-5f370af0e5954fdabf70aa3111bbcb4b
Source dataset
uspto-grants-2007_12
Patent number
US07304064B2

Reaction notes

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