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Dimethylformamide → Ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate

HRID 649398
Notes
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Reaction equation

HRID 649398 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[CH2:29](I)[CH3:30].CN(C)C=O>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:29][CH3:30])=[O:22])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340Iodoethane2×HCID 516892Sodium BicarbonateHCID 201437225-(1-Benzyloxycarbonyl-4-piperidyl)valeric acid

Product 1

HCID 14046929Ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 54.8 g of 5-(1-benzyloxycarbonyl-4-piperidyl)valeric acid, 29 g of sodium hydrogen-carbonate, 21 ml of ethyl iodide and 150 ml of N,N-dimethylformamide is heated at 70° to 80° C. with stirring for 3 hours. Ethyl iodide (10 ml) is additionally added to the reaction solution, followed by heating at 90° to 100° C. for 3 hours. After cooling, 1 l of water is added to the reaction solution, and the mixture is extracted with 1 l of ethyl acetate. The extract is washed with water, 1N hydrochloric acid and dilute aqueous sodium hydrogencarbonate solution successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 58 g of ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate as pale yellow oil.

Workup

  1. temperatureis heated at 70° to 80° C.
  2. temperatureby heating at 90° to 100° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with 1 l of ethyl acetate
  5. washThe extract is washed with water, 1N hydrochloric acid and dilute aqueous sodium hydrogencarbonate solution successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0450fa34024d40e7bff90e2f3ff6f900
Source dataset
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04739066

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes