Piperidine → Ethyl 4-(3-Piperidin-1-ylpropoxy)benzoate

HRID 268702Notes

Reaction equation

HRID 268702 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC.CCOC(C)=O.[I-].[K+]>[N:17]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 10340Sodium CarbonateHCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 17986307Ethyl 4-(3-Piperidin-1-ylpropoxy)benzoate

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of ethyl 4-(3-chloropropoxy)benzoate (4.73 g) (D. A. Walsh et al J. Med. Chem. 1989, 32(1), 105), piperidine (2.9 ml), sodium carbonate (3.1 g) and potassium iodide (162 mg) in 1-butanol (50 ml) was heated at 105° C. for 16 h. The reaction was cooled to rt, diluted with EtOAc (100 ml), washed with water (3×50 ml), saturated brine (50 ml), dried (MgSO4) and evaporated to give the title compound (D1) (6.88 g). MS electrospray (+ion) 292 (MH+). 1H NMR δ (CDCl3): 7.98 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=8.8 Hz), 4.34 (2H, q, J=7.5 Hz), 4.06 (2H, t, J=6.3 Hz), 2.46 (4H, m), 2.00 (2H, m), 1.50 (6H, m), 1.38 (3H, t, J=7.5 Hz).

Workup

  1. washwashed with water (3×50 ml), saturated brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-ce5f89bec97a4fc8a271ec7d10f9e872
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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