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2-[2-Chloro-5-((R)-3-ethoxycarbonyl-piperidin-1-yl)-phenyl]-benzoimidazole-1-carboxylic acid tert-butyl ester → (R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid ethyl ester

HRID 77070
Notes
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Reaction equation

HRID 77070 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24]2)[CH:20]=[CH:19][C:18]=1[Cl:34])=O)(C)(C)C>ClCCl.Cl.CCOCC>[CH2:32]([O:31][C:29]([C@@H:25]1[CH2:26][CH2:27][CH2:28][N:23]([C:21]2[CH:20]=[CH:19][C:18]([Cl:34])=[C:17]([C:9]3[NH:8][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[N:10]=3)[CH:22]=2)[CH2:24]1)=[O:30])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 669775292-[2-Chloro-5-((R)-3-ethoxycarbonyl-piperidin-1-yl)-phenyl]-benzoimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 66977797(R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid ethyl esterYield 78.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

Method 2—Step d To a mixture of 2-[2-Chloro-5-((R)-3-ethoxycarbonyl-piperidin-1-yl)-phenyl]-benzoimidazole-1-carboxylic acid tert-butyl ester (1.30 g, 2.68 mmol) in dichloromethane (2 mL), 2M HCl in Et2O (10 mL) was added and the resulting mixture was stirred overnight at room temperature. The solid was filtered off, then recovered with 10% NaOH (10 mL) and extracted with dichloromethane (3×10 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure, to get 0.81 g of the title compound without further purifications (85%).

Workup

  1. additionwas added
  2. filtrationThe solid was filtered off
  3. customrecovered with 10% NaOH (10 mL)
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d012fb04f32c49acb5f3ffcbc5076adc
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835648B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes