Hydrogen Bromide → gamma-Morpholinobutyric acid hydrobromide

HRID 267339Notes

Reaction equation

HRID 267339 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=[O:11])[CH2:3][CH2:2]1.[BrH:14]>O>[BrH:14].[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 44858Methyl 4-morpholinobutanoate

Product 1

HCID 68121683gamma-Morpholinobutyric acid hydrobromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 g. (0.052 mole) of Methyl γ-morpholinobutyrate (Cruickshank and Sheehan, J. Am. Chem. Soc. 83, 2891 (1961)) was dissolved in a mixture of 45 ml. of 47% hydrobromic acid and 45 ml. of water and heated for 16 hours at reflux. The solution was taken to dryness under reduced pressure, and the solid which formed was triturated with acetone. The material was filtered and crystallized from 60 ml. of acetic acid to give 12.4 g. (95%) of product as colorless crystals, m.p. 151°-152.5°C. The infrared and nuclear magnetic resonance spectra were consistent with the proposed structure.

Workup

  1. temperatureat reflux
  2. customthe solid which formed
  3. customwas triturated with acetone
  4. filtrationThe material was filtered
  5. customcrystallized from 60 ml
  6. customof acetic acid to give 12.4 g

Sources & evidence

ORD record
ord-b6f5b4f513de4a1696a4503087708966
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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