5-Methyl-2-pyrrolidone → HCID 19385515, compound

HRID 2399382Notes

Reaction equation

HRID 2399382 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[CH2:21]Cl)[CH2:13][CH2:12]1)[CH3:3].[C:26]1(=[O:32])[NH:31][CH:29]([CH3:30])[CH2:28][CH2:27]1.[Li]CCCC.CCCCCC>C1COCC1>[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH2:21][N:31]3[CH2:29][CH2:30][CH2:28][CH2:27][C:26]3=[O:32])[CH:23]=[CH:24][CH:25]=2)[CH2:13][CH2:12]1)[CH3:3]

Participants

5

Reactant 3

HCID 660555-Methyl-2-pyrrolidoneHCID 19385511HCID 19385511, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 19385515HCID 19385515, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[[1-[2-(1-methylethoxy)phenyl]-4-piperidinyl]methyl]benzyl chloride (5.25 g, 0.0147 mol) in THF (90 mL) was added dropwise to a solution of γ-valerolactam (2.06 g, 0.02 mol) in THF (50 mL) which had been treated at 0° C. with 1.6M n-BuLi/hexane (12 mL, 1 mol equiv). The resulting solution was heated to reflux for 3 h, cooled, and quenched with MeOH (20 mL). The solution was evaporated to dryness to give a yellow oil. The residue was chromatographed on silica gel using 99:1/CHCl3 :MeOH as eluant to give 1-[[3-[[1-[2-(1-methylethoxy)phenyl]-4-piperidinyl]methyl]phenyl]methyl]-piperidin-2-one as a light yellow oil, 1.41 g (23%). MS (Cl CH4): m/e 421 (MH+). 1H NMR (CDCl3): δ1.3 (d, 6H), 1.8 (m, 4H), 2.0 (m, 2H), 2.4 (s, 1H), 2.9 (m, 3H), 3.2 (m, 2H), 3.6 (s, 1H), 3.7 (d, 1H), 4.6 (m, 3H), 5.0 (s, 1H), 6.9 (m, 2H), 7.1 (m, 2H), 7.3-7.6 (m, 4H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 3 h
  3. temperaturecooled
  4. customquenched with MeOH (20 mL)
  5. customThe solution was evaporated to dryness
  6. customto give a yellow oil
  7. customThe residue was chromatographed on silica gel using 99:1/CHCl3

Sources & evidence

ORD record
ord-e7b018e845b945a1827c53bee09fc98e
Source dataset
uspto-grants-1995_09
Patent number
US05449677

Reaction notes

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