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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18945197, compound

HRID 399809
Notes
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Reaction equation

HRID 399809 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:13]=1)[C:8]([OH:10])=O)=[O:4].[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl>[OH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:8]([C:7]2[CH:6]=[C:5]([CH:13]=[C:12]([N:14]3[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH:11]=2)[C:3]([O:2][CH3:1])=[O:4])=[O:10])[CH2:22][CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 79341Piperidin-4-olHCID 18945316HCID 18945316, compound

Product 1

HCID 18945197HCID 18945197, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a mixture of 3-methoxycarbonyl-5-(pyrrol-1-yl)-benzoic acid (3.0 g), 4-hydroxypiperidine (1.23 g) and 1-hydroxybenzotriazole (1.81 g) in dichloromethane (100 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.57 g) under ice cooling, and the solution was stirred for 30 hours at room temperature. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution under stirring. The organic layer was successively washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (50:1). The fractions containing the desired product were collected and evaporated in vacuo to afford methyl 3-[(4-hydroxypiperidin-1-yl)carbonyl]-5-(pyrrol-1-yl)benzoate (3.56 g).

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate
  3. stirringa saturated aqueous sodium hydrogencarbonate solution under stirring
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (50:1)
  8. additionThe fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-6f02db630cdf43c2ab9c7aaa6432c167
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05824691

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes