1,2-Dichloroethane → HCID 12294579, compound

HRID 1716417Notes

Reaction equation

HRID 1716417 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)CCl.[CH:17]1[CH:18]=CC2N(O)N=[N:23][C:21]=2[CH:22]=1.CCN(CC)CC.N1CCCC1>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:23]1[CH2:18][CH2:17][CH2:22][CH2:21]1)=[O:12]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 72899Indole-2-carboxylic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 12294579HCID 12294579, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.300 g (1.86 mmol) of 1H-indole-2-carboxylic acid in CH2Cl2 (10 ml) was added 0.428 g (2.23 mmol) of EDC, 0.302 g (2.23 mmol) of HOBt, 0.28 ml (2.04 mmol) of Et3N and 0.17 ml (2.04 mmol) of pyrrolidine. The reaction mixture was stirred at RT over the night and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Re-crystallization in Et2O afforded 0.31 g (78%) of (1H-indol-2-yl)-pyrrolidin-1-yl-methanone as white crystals.

Workup

  1. additionpoured onto water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a309e81c54ce4452a32f41b064d450ca
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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