Potassium Carbonate → N-(Methoxycarbonylbutyl)-4-benzylpiperidine

HRID 324530Notes

Reaction equation

HRID 324530 reaction equation
Br[CH:2]([CH2:7][CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].[CH2:10]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:6][O:5][C:3]([CH2:2][CH2:7][CH2:8][CH2:9][N:20]1[CH2:21][CH2:22][CH:17]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:18][CH2:19]1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 529992Methyl 2-bromopentanoate

Product 1

HCID 54165409N-(Methoxycarbonylbutyl)-4-benzylpiperidineYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl bromovalerate (1.56 g, 8.0 mmol), 4-benzylpiperidine (1.49 g, 8.5 mmol) and potassium carbonate (2.93 g, 21.25 mmol) in 30 mL of acetonitrile was refluxed under N2 for 12 hr. The inorganic salt was removed through a short column of silica gel and washed with ethyl acetate (3×30 mL). The filtrate was evaporated in vacuo to give a residue, which was purified by flash chromatography, giving 1.8 g (78%) of the product as a pale yellow oil. 1H NMR (CHCl3), 1.312 (m, 2 H), 1.505-1.593 (m, 7 H), 1.831 (m, 2 H), 2.292 (m, 4 H), 2.505 (d, J=6.9 Hz, 2H), 2.860 (d, J=11.4 Hz, 2 H), 3.647 (s, 3 H), 7.136 (m, 5 H).

Workup

  1. temperaturewas refluxed under N2 for 12 hr
  2. customThe inorganic salt was removed through a short column of silica gel
  3. washwashed with ethyl acetate (3×30 mL)
  4. customThe filtrate was evaporated in vacuo
  5. customto give a residue, which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-6448c5f9122a49b6a3c936cf92027334
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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