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

HRID 604291Notes

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]

Participants

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

temperatureAfter cooling to room temperature
filtrationthe mixture is filtrated
concentrationAfter concentration in vacuo
extractionthe mixture is extracted with AcOEt
washwashed with brine
dry with materialdried over sodium sulfate
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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