Ethyl Bromide → Ethyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

HRID 507865Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:27][CH3:28]>CO>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:14]([O:16][CH2:27][CH3:28])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Benzyl-4-phenylamino-piperidine-4-carboxylic acid (40.1 g, 0.13 mol) and NaOH (5.12 g, 0.13 mol) was dissolved in methanol (1000 mL). The mixture was heated to reflux for 0.5 h. Then the solvent was removed under reduced pressure. The residue was dissolved in HMPT (300 mL). Bromo-ethane (17.44, 0.16 mol) was added at 20° C. The mixture was stirred overnight at 20° C. The reaction mixture was poured into ice-water and extracted with EtOAc (3×400 mL). The combined organics were washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue was purified by silicagel column chromatography (Petroleum ether./EtOAc 2:1) to give ethyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate.

Workup

temperatureThe mixture was heated
temperatureto reflux for 0.5 h
customThen the solvent was removed under reduced pressure
dissolutionThe residue was dissolved in HMPT (300 mL)
extractionextracted with EtOAc (3×400 mL)
washThe combined organics were washed with brine
dry with materialdried over Na2SO4
customevaporated under vacuum
customThe residue was purified by silicagel column chromatography (Petroleum ether./EtOAc 2:1)

Sources & evidence

ORD record: ord-c36e220092ae4dc49d5e977ae76903d6
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786308B2

Reaction notes

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