1,2-Dichloroethane → HCID 9901766, compound

HRID 2184926Notes

Reaction equation

HRID 2184926 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH2:17]([N:19]([CH2:22]C)[CH2:20][CH3:21])C.[CH2:24](Cl)[CH2:25]Cl.[OH2:28]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:22][N:19]([CH3:17])[CH2:20][CH2:21][CH2:24][C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:28]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 85883-Amino-9-ethylcarbazole

Product 1

HCID 9901766HCID 9901766, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-9-ethylcarbazole (500 mg, 2.38 mol), 3-(dimethylamino)butyric add (438 mg, 2.62 mmol, 1.1 equiv), triethylamine (0.398 mL, 289 mg, 2.85 mmol, 1.2 equiv) and DMAP (145 mg, 0.5 equiv) in CH2Cl2 (10 mL) was added EDC (500 mg, 2.62 mmol). The resultant solution was maintained at room temperature for 19 hours, and then poured into water and extracted with CH2Cl2 (2×25 ml). The combined organics were washed with water (1×25 ml), dried over anhydrous Na2SO4 and concentrated. Purification of the residue by flash column chromatography 10% MeOH/CH2Cl2 grading to 2% ammonium hydroxide/10% MeOH/CH2Cl2) provided 4-dimethylamino-N-(9-ethyl-9H-carbazol-3-yl)-butyramide (595 mg, 77%) as a tan foam.

Workup

  1. extractionextracted with CH2Cl2 (2×25 ml)
  2. washThe combined organics were washed with water (1×25 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customPurification of the residue by flash column chromatography 10% MeOH/CH2Cl2 grading to 2% ammonium hydroxide/10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e28a9be75a38466eb543566d12ee1f55
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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