Chloride → HCID 70147056, compound

HRID 2304545Notes

Reaction equation

HRID 2304545 reaction equation
[Cl-:1].Cl.[NH:3]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:4]1[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([O-])([O-])=O.[K+].[K+].CCO[CH2:23][CH3:24]>CN(C=O)C>[Cl:1][C:4]1[CH:5]=[C:23]([CH2:24][N:3]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:4]2[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 12436225Ethyl piperidine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 70147056HCID 70147056, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3thlorobenzyl chloride (11 mmol, 1.4 mL), ethyl pipecolinate hydrochloride (10 mmol, 1.94 g) and K2CO3 (12 mmol, 1.69 g) in DMF (10 mL) was stirred at 60° C. for 3 days. It was then diluted with ether (50 mL) and filtered. The filtrate was concentrated in vacuo to give ethyl N-(3chlorophenylmethyl)pipecolinate as a yellow oil (2.79g): 1H NMR (300 MHz) δ 7.21-7.35 (m, 4 H), 4.20 (q, J=7.1 Hz, 2 H), 3.77 (d, J=13.6 Hz, 1 H), 3.37 (d, J=13.6 Hz, 1 H), 3.14 (dd, J=7.5 Hz, 4.6 Hz, 1 H), 2.92 (dt, J=11.9, 5.4 Hz, 1 H), 2.15 (m, 1 H), 1.34-1590 (m, 6 H), 1.29 (t, J=7.1 Hz, 3 H); 13C NMR δ 173.74 (s), 140.73 (s), 134.06 (s), 129.35 (d), 128.99 (d), 127.14 (d), 64.33 (d), 60.34 (t), 59.98 (t), 50.11 (t), 29.52 (t), 25.25 (t), 22.39 (t), 14.30 (q); MS (FAB) 282 (98, M+H), 208 (100); HRMS (FAB) m/e calcd for (C15H20ClNO2+H) 282.1261, found 282.1248.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cadaaab6932d447483c41e51cfb7525a
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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