Oxalyl chloride → 4-(Piperidin-1-yl)-but-2-enoic acid anhydride dihydrochloride

HRID 566893Notes

Reaction equation

HRID 566893 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=O.[ClH:7].[N:8]1([CH2:14][CH:15]=[CH:16][C:17]([OH:19])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>ClCCl.CN(C)C=O>[ClH:4].[ClH:7].[N:8]1([CH2:14][CH:15]=[CH:16][C:17]([O:19][C:1](=[O:5])[CH:2]=[CH:15][CH2:14][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 698441674-Piperidin-1-yl-but-2-enoic acid-HCl

Product 1

HCID 881386014-(Piperidin-1-yl)-but-2-enoic acid anhydride dihydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.2 ml) was added to a stirred solution of 4-(piperidin-1-yl)-but-2-enoic acid hydrochloride (10 g) in dichloromethane (200 ml). Dimethylformamide (2 drops) was then added. The resultant suspension was stirred for 4 h and then concentrated to ˜25 ml. The slurry obtained was stirred a further 1 h and then filtered. The filter pad was washed with dichloromethan (50 ml) and dired in vacuo to give the title compound as a white solid (4.95 g). M.p. 120-124° C. (decomposition).

Workup

  1. concentrationconcentrated to ˜25 ml
  2. customThe slurry obtained
  3. filtrationfiltered
  4. washThe filter pad was washed with dichloromethan (50 ml) and dired in vacuo

Sources & evidence

ORD record
ord-5cca4da45abf4a739bf9368e6d91cd46
Source dataset
uspto-grants-2001_01
Patent number
US06177425B1

Reaction notes

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