Diethylamine → HCID 66692642, compound

HRID 1629587Notes

Reaction equation

HRID 1629587 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:23]2[CH2:22][CH2:21][CH2:20][CH:19]([C:24](Cl)=[O:25])[C:18]=2[C:17]2[C:12]1=[C:13]([Cl:29])[CH:14]=[CH:15][C:16]=2[O:27][CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>ClCCl>[CH2:30]([N:32]([CH2:33][CH3:34])[C:24]([CH:19]1[C:18]2[C:17]3[C:12](=[C:13]([Cl:29])[CH:14]=[CH:15][C:16]=3[O:27][CH3:28])[N:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:23]=2[CH2:22][CH2:21][CH2:20]1)=[O:25])[CH3:31]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86762562HCID 86762562, compound

Product 1

HCID 66692642HCID 66692642, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

9-(2-Benzyloxy-ethyl)-8-chloro-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride (8) (1.6 g, 3.7 mmol) was then dissolved in dichloromethane (50 mL), cooled to 0° C., stirred and diethylamine (810 mg, 11.0 mmol, 1.1 mL) was added dropwise. The reaction was allowed to warm to room temperature over a period of 18 h. The reaction mixture was then washed with 10% aqueous potassium carbonate (50 mL), separated, dried over magnesium sulfate and concentrated in vacuo to a gum. The crude material was crystallized from diethyl ether to afford 1.2 g (71%) of 9-(2-Benzyloxy-ethyl)-8-chloro-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide (9) as a white crystalline solid. The structure was confirmed by 13C NMR (75 MHz; CDCl3): δC 13.0, 14.5, 19.8, 22.2, 27.9, 36.4, 40.4, 41.9, 43.8, 55.0, 70.8, 73.3, 100.2, 108.5, 108.6, 119.9, 122.5, 127.4, 127.5, 128.3, 131.5, 137.8, 138.2, 152.4, and 174.5.

Workup

  1. temperatureto warm to room temperature over a period of 18 h
  2. washThe reaction mixture was then washed with 10% aqueous potassium carbonate (50 mL)
  3. customseparated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a gum
  6. customThe crude material was crystallized from diethyl ether

Sources & evidence

ORD record
ord-148db029117e45b0b910c5165eb14efc
Source dataset
uspto-grants-2014_07
Patent number
US08790619B2

Reaction notes

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