Diethylamine → HCID 57394572, compound

HRID 1506685Notes

Reaction equation

HRID 1506685 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH:12]([C:17](Cl)=[O:18])[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][C:9]=2[O:20][CH3:21].[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>ClCCl>[CH2:22]([N:24]([CH2:25][CH3:26])[C:17]([CH:12]1[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[O:20][CH3:21])[N:4]([CH2:3][CH2:2][F:1])[C:16]=2[CH2:15][CH2:14][CH2:13]1)=[O:18])[CH3:23]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86652111HCID 86652111, compound

Product 1

HCID 57394572HCID 57394572, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-(2-fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride (18) (371 mg, 1.2 mmol) was dissolved in dichloromethane (2 mL) and cooled to 0° C. diethylamine (177 mg, 2.4 mmol, 250 μL) was then added and the reaction was stirred overnight at RT. The reaction was quenched with 10% aqueous potassium carbonate (2 mL). The dichloromethane layer was collected through a phase separator then concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A): ethyl acetate (B) (50-100% (B), 50 g, 35.2 CV, 40 mL/min) to afford a pale yellow solid. The solid was next triturated with a minimum amount of diethyl ether to afford 240 mg (58%) of 9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethyl amide (non-radioactive imaging agent 5). The structure was confirmed by 13C NMR (75 MHz, CDCl3): δC 13.0, 14.6, 19.9, 21.9, 28.0, 36.3, 40.5, 41.9, 43.1 (d, TCF=23 Hz), 54.7, 82.0 (d, TCF=173 Hz), 99.7, 102.1, 108.3, 117.0, 121.5, 135.3, 137.4, 153.3, and 174.8.

Workup

  1. additionwas then added
  2. customThe reaction was quenched with 10% aqueous potassium carbonate (2 mL)
  3. customThe dichloromethane layer was collected through a phase separator
  4. concentrationthen concentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with petrol (A)
  7. customethyl acetate (B) (50-100% (B), 50 g, 35.2 CV, 40 mL/min) to afford a pale yellow solid
  8. customThe solid was next triturated with a minimum amount of diethyl ether

Sources & evidence

ORD record
ord-f9c7ce8b5b004eb0a45e4b10187fed32
Source dataset
uspto-grants-2015_12
Patent number
US09220795B2

Reaction notes

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