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Hydrochloric Acid → 1'-(4-Amino-3-methoxy-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester

HRID 604291
Notes
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Reaction equation

HRID 604291 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[C:22]([O:29][CH3:30])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(OCC)(=O)C>C(O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([O:29][CH3:30])[CH:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 598602671'-(3-Methoxy-4-nitro-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester

Product 1

HCID 598492031'-(4-Amino-3-methoxy-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl esterYield 95.3%

Reagents, catalysts & solvents 2

HCID 23925
Iron
Catalyst
HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1′-(3-Methoxy-4-nitro-phenyl)-[4,4′]bipiperidinyl-1-carboxylic acid tert-butyl ester (2.0 g, 4.77 mmol), iron powder (1.33 g, 23.85 mmol), 1N hydrogen chloride (9.54 mL, 9.54 mmol) in ethanol (50 mL) is stirred at 80° C. for 3 h. After cooling to room temperature, 2N hydrogen chloride (5 mL) and ethyl acetate are added and then the mixture is filtrated. After concentration in vacuo, the mixture is extracted with AcOEt, washed with brine, dried over sodium sulfate and evaporated to give 1′-(4-Amino-3-methoxy-phenyl)-[4,4′]bipiperidinyl-1-carboxylic acid tert-butyl ester (1.77 g, 95% yield) as pale purple solids.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtrated
  3. concentrationAfter concentration in vacuo
  4. extractionthe mixture is extracted with AcOEt
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-b5e3df4643304464ac7317b766b395ae
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes