Water → (S)-N-(1-(2-(4-fluorophenyl)ethyl)pyrrolidin-3-yl)carbazole-9-carboxamide

HRID 992321Notes

Reaction equation

HRID 992321 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[CH:23]1[C:35]2[N:34]([C:36](Cl)=[O:37])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1.O>C(Cl)Cl>[F:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:36]([N:34]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:27]4[C:35]3=[CH:23][CH:24]=[CH:25][CH:26]=4)=[O:37])[CH2:3]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 32622619H-carbazole-9-carbonyl chlorideHCID 59915932(S)-3-amino-1-(2-(4-fluorophenyl)ethyl)pyrrolidine

Product 1

HCID 59915920(S)-N-(1-(2-(4-fluorophenyl)ethyl)pyrrolidin-3-yl)carbazole-9-carboxamideYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-Amino-1-(2-(4-fluorophenyl)ethyl)pyrrolidine (0.42 g) and triethylamine (0.28 ml) were dissolved in methylene chloride (10 ml), and carbazole-N-carbonyl chloride (0.46 g) was added under ice-cooling. After the completion of the reaction, water was added, and the mixture was extracted with chloroform and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and IPE was added to the obtained residue. The precipitated crystals were collected by filtration to give (S)-N-(1-(2-(4-fluorophenyl)ethyl)pyrrolidin-3-yl)carbazole-9-carboxamide (0.38 g), melting point 107-108° C.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure, and IPE
  6. additionwas added to the obtained residue
  7. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ab740070f33740d788554ab8d6293b5f
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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