Water → HCID 18408857, compound

HRID 993040Notes

Reaction equation

HRID 993040 reaction equation
Cl.Cl.[O:3]=[C:4]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:7][CH2:6][N:5]1[CH2:16][C:17]([C:19]1[CH:33]=[CH:32][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])=[CH:21][CH:20]=1)=[O:18].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.Cl[C:51]([O:53][CH:54]([Cl:56])[CH3:55])=[O:52].O>C(Cl)Cl>[Cl:56][CH:54]([O:53][C:51]([N:13]1[CH2:12][CH2:11][CH:10]([N:8]2[CH2:7][CH2:6][N:5]([CH2:16][C:17]([C:19]3[CH:33]=[CH:32][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])=[CH:21][CH:20]=3)=[O:18])[C:4](=[O:3])[CH2:9]2)[CH2:15][CH2:14]1)=[O:52])[CH3:55]

Participants

6

Reactant 4

HCID 962WaterHCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 18408888HCID 18408888, compound

Product 1

HCID 18408857HCID 18408857, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 99.6 mg of n-butyl 4-[[2-oxo-4-(piperidin-4-yl)-piperazin-1-yl]acetyl]phenoxyacetate dihydrochloride synthesized according to the method described in WO962503 in 2 ml of methylene chloride were added 151 mg of proton sponge and 26 μl of 1-chloroethyl chloroformate with stirring at 0° C., and the mixture was stirred at room temperature for 18 hours. The reaction mixture thus obtained was poured into 2 ml of water, and extracted three times with 4 ml of ethyl acetate. The organic layer collected was dried over magnesium sulfate, and the solvent was removed by distillation to give 82.7 mg of n-butyl 4-[[4-[1-(1-chloroethyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetate as a crude crystalline product.

Workup

  1. customsynthesized
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. customThe reaction mixture thus obtained
  4. extractionextracted three times with 4 ml of ethyl acetate
  5. customThe organic layer collected
  6. dry with materialwas dried over magnesium sulfate
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-a77dc0790cdf47988334bde08db08db2
Source dataset
uspto-grants-2002_10
Patent number
US06472397B1

Reaction notes

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