Potassium Carbonate → tert-butyl 3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate

HRID 2085391Notes

Reaction equation

HRID 2085391 reaction equation
Cl.[NH:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH2:4][CH2:3]1.Br[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:15]([NH:14][C:10]1[CH:9]=[C:8]([C:5]2[CH2:6][CH2:7][N:2]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 22049291N-(3-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)acetamide hydrochloride

Product 1

HCID 21957172tert-butyl 3-(4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N1-[3-(1,2,3,6-tetrahydro-4-pyridinyl) phenyl]acetamide hydrochloride (8.24 mmol), tert-butyl N-(3-bromopropyl)carbamate and potassium carbonate (33 mmol) in dry dioxane (30 mL) was heated at reflux temperature overnight. The solids were removed by filtration, the solution was concentrated in vacuo and the product was chromatographed, giving the desired product (110 mg). 1H NMR δ 7.65 (s, 1 H), 6.98 (s, 1 H), 7.45 (d, 1 H, J=7.8 Hz), 7.16 (apparent t, 1 H, J=7.8 Hz), 7.10 (d, 1 H, J=7.8 Hz), 6.02 (s, 1 H), 5.23 (b, 1 H), 3.40 (b, 2 H), 3.30-1.80 (m, 10 H), 2.18 (s, 3 H), 1.45 (s, 9 H)

Workup

  1. temperatureat reflux temperature overnight
  2. customThe solids were removed by filtration
  3. concentrationthe solution was concentrated in vacuo
  4. customthe product was chromatographed

Sources & evidence

ORD record
ord-17dafb5f50354409b5512995f8eac5fc
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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