Diethyl Ether → 1-[4-(p-Chlorophenyl)-2-oxopyrrolidin-1-ylacetyl]-4-(2-oxopyrrolidin1-ylacetyl)-piperazine

HRID 2166347Notes

Reaction equation

HRID 2166347 reaction equation
Cl.[O:2]=[C:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10].C(N(CC)CC)C.ClC1C(O[C:32](=[O:47])[CH2:33][N:34]2[CH2:38][CH:37]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)[CH2:36][C:35]2=[O:46])=C(Cl)C(Cl)=C(Cl)C=1Cl.C(OCC)C>C(Cl)Cl>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([CH:37]2[CH2:38][N:34]([CH2:33][C:32]([N:14]3[CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH2:8][N:4]4[CH2:5][CH2:6][CH2:7][C:3]4=[O:2])[CH2:12][CH2:13]3)=[O:47])[C:35](=[O:46])[CH2:36]2)=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 230395351-[2-(2-Oxopyrrolidin-1-yl)-acetyl]-piperazine hydrochlorideHCID 539749662-[4-(p-Chlorophenyl)-2-oxopyrrolidin-1-yl]-acetic acid pentachlorophenyl ester

Product 1

HCID 230395251-[4-(p-Chlorophenyl)-2-oxopyrrolidin-1-ylacetyl]-4-(2-oxopyrrolidin1-ylacetyl)-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6.0 g (23.3 mmol) of 1-[2-(2-oxopyrrolidin-1-yl)-acetyl]-piperazine hydrochloride in 80 ml of methylene chloride there are added firstly 2.6 g (3.6 ml; 25.5 mmol) of triethylamine and then, dropwise, a solution of 13.7 g (23.3 mmol) of 2-[4-(p-chlorophenyl)-2-oxopyrrolidin-1-yl]-acetic acid pentachlorophenyl ester in 30 ml of methylene chloride. After being stirred at 20° for 16 hours, the suspension is filtered with suction. 6.16 g of a white crystalline mass are obtained. 110 ml of ethyl ether are stirred into the filtrate, whereby a further 6.51 g of precipitate can be formed and collected. The two portions are combined, triturated under 200 ml of ethyl ether and filtered with suction, and the resulting product is dissolved in 150 ml of hot glacial acetic acid, and warm water (50°) is added until the solution becomes cloudy. The whole is cooled to 20 °; after 3 hours, the resulting crystalline product is filtered off with suction and dried on a water bath. 1-[4-(p-chlorophenyl)-2-oxopyrrolidin-1-ylacetyl]-4-(2-oxopyrrolidin1-ylacetyl)-piperazine having a melting point of 224°-226° is obtained.

Workup

  1. filtrationthe suspension is filtered with suction
  2. custom6.16 g of a white crystalline mass are obtained
  3. customcan be formed
  4. customcollected
  5. customtriturated under 200 ml of ethyl ether
  6. filtrationfiltered with suction
  7. dissolutionthe resulting product is dissolved in 150 ml of hot glacial acetic acid
  8. temperaturewarm water (50°)
  9. additionis added until the solution
  10. temperatureThe whole is cooled to 20 °
  11. waitafter 3 hours
  12. filtrationthe resulting crystalline product is filtered off with suction
  13. customdried on a water bath

Sources & evidence

ORD record
ord-d1d9b426c39e4edfa88a0dc0ee3126e0
Source dataset
uspto-grants-1990_07
Patent number
US04945092

Reaction notes

Loading…