Diethyl Ether → HCID 15651179, compound

HRID 1654102Notes

Reaction equation

HRID 1654102 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][O:9][C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1)=[O:11].[CH2:18](OCC)C>>[CH2:6]([O:5][C:3]([CH2:2][N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([C:10]([O:9][CH2:8][CH3:18])=[O:11])[CH2:13]1)=[O:4])[CH3:7]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 351626Methyl piperidine-3-carboxylate

Product 1

HCID 15651179HCID 15651179, compound

Procedure

Ethyl bromoacetate (21.2 g, 0.127 mol) was added dropwise to a solution of 3-methoxycarbonylpiperidine (40 g, 0.254 mol) in diethyl ether (250 ml) at 0° C. The reaction was heated under reflux for 1 hour and the resulting precipitate filtered off and washed with diethyl ether. The ethereal solution was concentrated under reduced pressure to give the title compound (27.6 g); δ (60 MHz, CDCl3) 1.25 and 1.27 (each 3H, each t, J=7 Hz, 2×OCH2CH3). 1.40-3.70 (9H, m, 2CH2, 3CH, 4CH2, 5CH2 and 6CH2), 3.20 (2H, s, NCH2CO2), 4.10 and 4.15 (each 2H, each q, J=7 Hz, 2×NCH2CO2).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationthe resulting precipitate filtered off
  4. washwashed with diethyl ether
  5. concentrationThe ethereal solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea9687c6da534828b1902f113e909f9e
Source dataset
uspto-grants-1995_04
Patent number
US05405853

Reaction notes

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