Hydrogen Bromide → gamma-Morpholinobutyric acid hydrobromide

HRID 2398885Notes

Reaction equation

HRID 2398885 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°. The infrared and nmr spectra are consistent with the proposed structure.

Workup

  1. dissolution83, 2891 (1961) was dissolved in a mixture of 45 ml
  2. temperatureat reflux
  3. customthe solid which formed
  4. customwas triturated with acetone
  5. filtrationThe material was filtered
  6. customcrystallized from 60 ml
  7. customof acetic acid to give 12.4 g

Sources & evidence

ORD record
ord-2bfa2a129a5a4272bac73557281a64ed
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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