Diethyl Ether → Ethyl 5-(morpholin-4-yl)pentanoate

HRID 255019Notes

Reaction equation

HRID 255019 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C.C(OCC)C>C(O)C>[N:11]1([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8083MorpholineHCID 8471TriethylamineHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 16097789Ethyl 5-(morpholin-4-yl)pentanoateYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-bromovalerate (8 g, 38.3 mmole), morpholine (3.67 g, 42 mmole) and triethylamine (4.2 g, 42 mmole) in ethanol (100 mL) was heated to reflux overnight. The solution was concentrated to afford a gummy white solid which was mixed with diethyl ether and filtered to remove the solid. The filtrate was washed with saline (3×50 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford 7.1 g (87%) of ethyl 5-morpholin-4-ylpentanoate as a pale brown liquid. MS (m/z, ES+): 217 (M+2, 100%), 216 (M+1, 57%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationThe solution was concentrated
  4. customto afford a gummy white solid which
  5. filtrationfiltered
  6. customto remove the solid
  7. washThe filtrate was washed with saline (3×50 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04c47cfb0cc1467aad2ac7d7661617ea
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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