Potassium Carbonate → Tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamate

HRID 1832141

Reaction equation

HRID 1832141 reaction equation
[NH:1]1[CH2:6][CH2:5][CH: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.Br[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+].C(N(C(C)C)CC)(C)C>O1CCOCC1>[C:14]([NH:13][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][N:1]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:2][CH2:3]2)[CH:12]=[CH:11][CH:10]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 22048943Acetamide, N-[3-(4-piperidinyl)phenyl]-

Product 1

HCID 22049023Tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamateYield 431.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N1-[3-(4-piperidyl)phenyl]acetamide (550 mg, 0.210 mmol), tert-butyl N-(3-bromopropyl)carbamate (550 mg, 0.230 mmol), K2CO3 (1.10 g, 0.890 mmol), diisopropylethyl amine (1.50 mL) and a few crystals of KI in dioxane (20 mL) was heated at reflux temperature for 2 days. The precipitated salts were removed by filtration, concentrated in vacuo and the crude product was chromatographed, giving the desired product (340 mg): 1H NMR (CDCl3) δ 8.15 (s, 1H), 7.47–7.44 (m, 2H), 7.22 (t, 1H, J=7.8 Hz), 6.94 (d, 1H, J=7.8 Hz), 5.53 (b, 1H), 3.23 (b, 6H), 2.80–1.60 (m, 9H), 2.20 (s, 3H), 1.45 (s, 9H).

Workup

  1. temperatureat reflux temperature for 2 days
  2. customThe precipitated salts were removed by filtration
  3. concentrationconcentrated in vacuo
  4. customthe crude product was chromatographed

Sources & evidence

ORD record
ord-8f7157743da3488aa67cab414195402e
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Linked notes

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