Triethylamine → (4-Chloro-phenyl)-(2,5-dihydro-pyrrol-1-yl)-methanone

HRID 1868520Notes

Reaction equation

HRID 1868520 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]=[CH:2]1.CCN(CC)CC.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C1COCC1.CN(C1C=CN=CC=1)C.CCOCC>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:1]2[CH2:5][CH:4]=[CH:3][CH2:2]2)=[O:19])=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 94395Pyrroline

Product 1

HCID 57982288(4-Chloro-phenyl)-(2,5-dihydro-pyrrol-1-yl)-methanoneYield 91.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Pyrroline (4 mL, 54 mmol) was dissolved in THF (100 mL), Et3N (14 mL, 100 mmol) was added. The mixture was cooled to 0° C. 4-chloro-benzoyl chloride (7.6 mL, 60 mmol) was added very slowly at 0° C. Catalytic amount of DMAP was added too. Finally the reaction mixture was stirred at 0° C. to RT for overnight. The reaction mixture was diluted with ether and filtered to remove white solid of Et3N.HCl. Then evaporated to remove solvent and triturated with hexane/ether to give white solid 10.3 g with ratio of unsaturated/saturated about 3/1 by NMR. Then triturated with hexane/ether again to give 6.68 g white solid with ratio of unsaturated/saturated about 3.7/1 by NMR. 1H-NMR (300 MHz, CDCl3): δ 4.3 (4H, d), 5.80 (2H, d), 7.40 (4H, dd)

Workup

  1. filtrationfiltered
  2. customto remove white solid of Et3N.HCl
  3. customThen evaporated
  4. customto remove solvent
  5. customtriturated with hexane/ether

Sources & evidence

ORD record
ord-d50daa7277c9435492084be62f567ecb
Source dataset
uspto-grants-2009_12
Patent number
US07635698B2

Reaction notes

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