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

HRID 1832137Notes

Reaction equation

HRID 1832137 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.Cl.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:14]([NH:13][C:9]1[CH:8]=[C:7]([C:4]2[CH2:5][CH2:6][N:1]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:2][CH:3]=2)[CH:12]=[CH:11][CH:10]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 21957228N-(3-(1,2,3,6-Tetrahydropyridin-4-yl)phenyl)acetamide

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.HCl (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 chromatograghed, giving the desired product (110 mg). 1H NMR (CDCl3) δ 7.65 (s, 1H), 6.98 (s, 1H), 7.45 (d, 1H, J=7.8 Hz), 7.16 (apparent t, 1H, J=7.8 Hz), 7.10 (d, 1H, J=7.8 Hz), 6.02 (s, 1H), 5.23 (b, 1H), 3.40 (b, 2H), 3.30–1.80 (m, 10H), 2.18 (s, 3H), 1.45 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-b3123c235fcd4475989117f374dfe412
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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