Bromoacetic Acid → 4-Morpholineacetic acid

HRID 604228Notes

Reaction equation

HRID 604228 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 (2 g, 14.4 mole) was dissolved in tetrahydrofuran (50 mL) and added dropwise to a stirred solution of morpholine (3.76 g, 43.2 mole) in tetrahydrofuran (THF, 20 mL). The solution was stirred at room temperature for three days. The white solid (4.17 g) was filtered, washed with THF (100 mL), and recrystallised from hot ethanol (EtOH), Yield: 2.59 g: IR: 1740 cm−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 (4.17 g) was filtered
  2. washwashed with THF (100 mL)
  3. customrecrystallised from hot ethanol (EtOH), Yield: 2.59 g

Sources & evidence

ORD record
ord-f206881978144b3f9ea6e75c7561e38a
Source dataset
uspto-grants-2011_03
Patent number
US07910059B2

Reaction notes

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