Triethylamine → Benzyl 4-pyridin-4-ylpiperidine-1-carboxylate

HRID 1785396Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:20](Cl)([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C([O-])(O)=O.[Na+]>>[N:10]1[CH:9]=[CH:8][C:7]([CH:4]2[CH2:5][CH2:6][N:1]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:2][CH2:3]2)=[CH:12][CH:11]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 10387Benzyl chloroformate

HCID 516892Sodium Bicarbonate

HCID 11395974-(4-Piperidyl)pyridine

Product 1

HCID 69053202Benzyl 4-pyridin-4-ylpiperidine-1-carboxylate

Procedure

A 10 mL round bottom flask was charged with piperidine 32 (500 mg, 3.08 mmol), and then triethylamine (314 mg, 3.10 mmol), and then CbzCl (529 mg, 3.10 mmol), and the reaction mixture was allowed to stir at room temperature for 12 hours. The reaction mixture was then poured into 50 mL of an aqueous solution saturated with NaHCO3 and extracted with 3×50 mL of methylene chloride. The organic fractions were pooled, dried over Na2SO4, filtered, concentrated under reduced pressure, and not purified further. Crude yield of 33: 900 mg (99%). 1H NMR (500 MHz, CDCl3) δ 1.87 (m, 2H), 2.30 (m, 2H), 2.69 (m, 1H), 2.91 (bs, 2H), 4.37 (bs, 2H), 5.17 (m, 2H), 7.13 (d, J=6.3 Hz, 2H), 7.39 (m, 5H), 8.54 (d, J=6.3 Hz, 2H).

Workup

extractionextracted with 3×50 mL of methylene chloride
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customnot purified further

Sources & evidence

ORD record: ord-834fce27d77a4e8384f0597fd5038b28
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504501B2

Reaction notes

Loading…