Triethylamine → HCID 59006332, compound

HRID 2378960Notes

Reaction equation

HRID 2378960 reaction equation
[N+:1]([C:4]1[C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=[CH:6][N:5]=1)([O-:3])=[O:2].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)C>[N+:1]([C:4]1[C:9]([CH2:10][CH2:11][NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 12682914-Amino-1-Boc-piperidine2×HCID 59006385HCID 59006385, compound

Product 1

HCID 59006332HCID 59006332, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2-Nitro-3-vinylpyridine (0.300 g, 2 mmol), tert-butyl 4-aminopiperidine-1-carboxylate (0.601 g, 3.00 mmol), and ethanol (5 ml) were combined. Triethylamine (0.836 ml, 6.00 mmol) was added. The vial was capped and heated at 90° C. for 62 hours. More tert-butyl 4-aminopiperidine-1-carboxylate (0.601 g, 3.00 mmol), and triethylamine (0.836 ml, 6.00 mmol) were added and the mixture was heated at 90° C. for 20 hours. Mixture was concentrated by roto-vap. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as tan solid in 48% yield. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 8.38 (dd, J=4.58, 1.53 Hz, 1 H) 7.84 (dd, J=7.63, 1.53 Hz, 1 H) 7.49 (dd, J=7.63, 4.58 Hz, 1 H) 3.92 (s, 2 H) 2.85-2.98 (m, 3 H) 2.75 (t, J=11.75 Hz, 2 H) 2.50-2.62 (m, 1 H) 1.75 (d, J=12.51 Hz, 2 H) 1.40 (s, 9 H) 1.00-1.27 (m, 4 H).

Workup

  1. customThe vial was capped
  2. temperaturethe mixture was heated at 90° C. for 20 hours
  3. concentrationMixture was concentrated by roto-vap
  4. washSilica gel chromatography eluting ethyl acetate-hexanes

Sources & evidence

ORD record
ord-89a2cae8075c46d2a4fd385faa359c25
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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