Triethylamine → 2-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetonitrile

HRID 1752247Notes

Reaction equation

HRID 1752247 reaction equation
Br[CH:2]1[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[CH2:8][C:9]#[N:10].Cl.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(#N)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH:22]2[CH2:27][CH2:26][N:25]([CH:5]3[CH2:6][CH2:2][N:3]([CH2:8][C:9]#[N:10])[C:4]3=[O:7])[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27405874-(4-Methoxybenzoyl)piperidine hydrochlorideHCID 893757442-(2-Bromo-5-oxopyrrolidin-1-yl)acetonitrile

Product 1

HCID 893757962-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetonitrileYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-bromo-5-oxopyrrolidin-1-yl)acetonitrile (730 mg, 3.6 mmol) and (4-methoxyphenyl)(piperidin-4-yl)methanone hydrochloride (920 mg, 3.6 mmol) in acetonitrile (4 mL) was added triethylamine (1.5 mL, 11 mmol). The mixture was microwave at 130° C. for 12 minutes. The solvent was removed in vacuo and the residue was taken up in methylene chloride and water. The organic layer was purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0) to provide slightly yellow oil (950 mg, 74% yield). 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J=8.5 Hz, 2H), 6.96 (d, J=8.5 Hz, 2H), 4.22-4.39 (m, 2H), 3.90 (s, 3H), 3.57 (dt, J=22.6, 9.0 Hz, 2H), 3.40-3.51 (m, J=8.5 Hz, 1H), 3.23-3.39 (br s, 1H), 2.93-3.20 (m, 3H), 2.33-2.61 (m, 2H), 2.13-2.31 (m, 1H), 1.83-2.03 (m, 4H). HRMS calculated for C13H23N3O3 342.1818. found (ESI, [M+H]+), 342.1830.

Workup

  1. customat 130° C.
  2. customfor 12 minutes
  3. customThe solvent was removed in vacuo
  4. customThe organic layer was purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0)

Sources & evidence

ORD record
ord-4de8130ef5d7465fb6d5ca1818822819
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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