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Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate → 4-(Dibenzylamino)-2-methylcyclopentanecarboxylic acid

HRID 1969749
Notes
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Reaction equation

HRID 1969749 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:9]1[CH2:13][CH:12]([C:14]([O:16]CC)=[O:15])[CH:11]([CH3:19])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.O1CCOCC1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]1[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH:11]([CH3:19])[CH2:10]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 58010318Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate

Product 1

HCID 585575354-(Dibenzylamino)-2-methylcyclopentanecarboxylic acidYield 98.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate (3.65 g, 10.38 mmol) was dissolved in a mixture of HCl (6 N aqueous, 20 mL) and 1,4-dioxane (50 mL) and the resulting mixture was heated at about 60° C. for about 72 h. The organic solvent was removed under reduced pressure. The aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 (40 mL) and extracted with EtOAc (50 mL). The organic phase was washed with brine (40 mL), dried over anhydrous MgSO4 and concd under reduced pressure to yield 4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid (3.3 g, 98%) as a white amorphous solid: LC/MS (Table 1, Method a) Rt=1.66 min; MS m/z 324 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. additionThe aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 (40 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic phase was washed with brine (40 mL)
  5. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure

Sources & evidence

ORD record
ord-afa26b44ac9740c7b73aac6c03b6b679
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426411B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes