4-Methyloxybenzyl chloride → HCID 2838202, compound

HRID 2304544Notes

Reaction equation

HRID 2304544 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.Cl.[NH:12]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:13]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:12]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:13]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 12436225Ethyl piperidine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 2838202HCID 2838202, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
62 °C

Procedure

4-Methoxy benzyl chloride (55 mmol, 8.61 g) was add ed t o a mixture of K2C3 (56 mmol, 7.7 4 g) and ethyl pipecolinate hydrochloride (50 mmol, 9.68 g) in DMF (55 mL). The mixture was stirred for 3 days at 62° C., and was filtered. Ice-cold HCl solution (1.5 N, 50 mL) was added to the filtrate and it was extracted with ether (3×100 mL). The aqueous phase was basified with NaOH solution (40%) and extracted with ether (5×100 mL). The combined extracts were washed with brine, dried with Na2SO4 and MgSO4 and concentrated in vacuo to give ethyl N-(4-methoxyphenylmethyl)-pipecolinate as a yellow oil (7.12 g): 1H NMR (300 MHz) δ 7.23 (d, J=8.6 Hz, 2 H), 6.84 (d, J=8.6 Hz, 2 H), 4.22 (q, J=7.1 Hz, 2 H), 3.70 (s, Me), 3.73 (d, J=13.1 Hz, 1 H), 3.34 (d, J=13.6 Hz, 1 H), 3.08 (dd, J=8.2, 4.3 Hz, 1 H), 2.93 (m, 1 H), 2.10 (m, 2 H), 1.80 (m, 2 H), 1.56 (m, 3 H), 1.30 (t, J=7.1 Hz, 3 H); 13C NMR δ 174.00, 158.68, 130.43, 130.01, 113.46, 64.55, 60.30, 59.87, 55.20, 50.15, 29.64, 25.24, 22.67, 14.33; MS (E) 277 (2, M), 204 (90), 121 (100); HRMS (EI) m/e calcd for C16H23NO3 277.1678, found 277.1682.

Workup

  1. filtrationwas filtered
  2. additionIce-cold HCl solution (1.5 N, 50 mL) was added to the filtrate and it
  3. extractionwas extracted with ether (3×100 mL)
  4. extractionextracted with ether (5×100 mL)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with Na2SO4 and MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f71ed7ab4ff34f5fa8f30dcb78c07019
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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