Bromoacetic Acid → 4-Morpholineacetic acid

HRID 1190780Notes

Reaction equation

HRID 1190780 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>O1CCCC1>[N:6]1([CH2:2][C:3]([OH:5])=[O:4])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6227Bromoacetic AcidHCID 8083Morpholine

Product 1

HCID 4389684-Morpholineacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Bromoacetic acid (2g, 14.4 mole) was dissolved in tetrahydrofuran (50mL) and added dropwise to a stirred solution of morpholine (3.76g, 43.2 mole) in tetrahydrofuran (THF, 20mL). The solution was stirred at room temperature for three days. The white solid (4.17g) was filtered, washed with THF (100mL), and recrystallised from hot ethanol (EtOH), Yield: 2.59g: IR:1740cm-1. For the two different isobaric versions of morpholine acetic acid, either bromoacetic-1-13C acid (Aldrich PN 27,933-1) or bromoacetic-2-13C acid (Aldrich PN 27,935-8) was substituted for bromoacetic acid.

Workup

  1. filtrationThe white solid (4.17g) was filtered
  2. washwashed with THF (100mL)
  3. customrecrystallised from hot ethanol (EtOH), Yield: 2.59g

Sources & evidence

ORD record
ord-95beaa267cc2429ca5272935d180dc1a
Source dataset
uspto-grants-2014_03
Patent number
US08679773B2

Reaction notes

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