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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(3-Cyclopenten-1-ylcarbonyl)-4-(3,4-dichlorophenoxy)piperidine

HRID 1727843
Notes
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Reaction equation

HRID 1727843 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5]N1CCCCC1.[CH:16]1[CH:17]=[CH:18]C2N(O)N=[N:22][C:20]=2[CH:21]=1.[CH:26]1([C:31]([OH:33])=O)[CH2:30][CH:29]=[CH:28][CH2:27]1.CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C.O>[CH:26]1([C:31]([N:22]2[CH2:18][CH2:17][CH:16]([O:5][C:4]3[CH:12]=[CH:13][C:14]([Cl:15])=[C:2]([Cl:1])[CH:3]=3)[CH2:21][CH2:20]2)=[O:33])[CH2:27][CH:28]=[CH:29][CH2:30]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 8537563-Cyclopentene-1-carboxylic acidHCID 685803253,4-Dichlorophenoxypiperidine

Product 1

HCID 689381871-(3-Cyclopenten-1-ylcarbonyl)-4-(3,4-dichlorophenoxy)piperidineYield 79.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3,4-Dichlorophenoxypiperidine (3.09 g) was dissolved in dichloromethane (80 mL). HOBT (1.77 g) and DMAP (0.44 g) were added followed by a solution of 3-cyclopentene-1-carboxylic acid (1.45 g) in dichloromethane (5 mL). EDCI (2.45 g) was added and the solution was stirred for 60 h. Water (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (2×40 mL). The organic phases were combined, dried (MgSO4), filtered and evaporated to give subtitle compound (3.40 g) that was used without further purification.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2×40 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-003c782868804755856599a9342dd79c
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495013B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes