1,4-Dioxane → (4-Chloro-phenyl)-[4-(4-hydroxy-pyrrolidin-3-yl)-piperazin-1-yl]-methanone

HRID 1868515Notes

Reaction equation

HRID 1868515 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)[CH2:9]1)=O)(C)(C)C.O1CCOCC1>C(Cl)Cl.CCOCC>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:17]2[CH2:18][CH2:19][N:14]([CH:10]3[CH:11]([OH:13])[CH2:12][NH:8][CH2:9]3)[CH2:15][CH2:16]2)=[O:28])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 669686813-[4-(4-Chloro-benzoyl)-piperazin-1-yl]4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66968375(4-Chloro-phenyl)-[4-(4-hydroxy-pyrrolidin-3-yl)-piperazin-1-yl]-methanoneYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3-[4-(4-Chloro-benzoyl)-piperazin-1-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester was dissolved in CH2Cl2. 4M HCL/dioxane (150 mL) was added. The mixture was stirred at RT for 4 h. White precipitate was formed. The mixture was diluted with ether, filtered. The white solid was washed with ether and dried to give desired product (99% yield). 1H-NMR (300 MHz, DMSO, HCl salt): δ 3.0-4.0 (m, 12 H), 4.85 (m, 2 H), 7.25 (d, 2 H), 7.54 (d, 2 H) Retention Time (LC method: formic acid polar): 1.01 min. MS (M+H+): 310

Workup

  1. customWhite precipitate was formed
  2. filtrationfiltered
  3. washThe white solid was washed with ether
  4. customdried

Sources & evidence

ORD record
ord-ce51395308e247b691d192af270458cd
Source dataset
uspto-grants-2009_12
Patent number
US07635698B2

Reaction notes

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