Glycolic Acid → HCID 20439386, compound

HRID 1979536Notes

Reaction equation

HRID 1979536 reaction equation
I.[NH2:2][NH:3][C:4]([NH:23][CH3:24])=[N:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:11]=1.[C:25](O)(=O)[CH2:26][OH:27]>C1C=CC=CC=1>[CH3:24][N:23]1[C:4]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[CH:11]=2)=[N:3][N:2]=[C:25]1[CH2:26][OH:27]

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 178484962HCID 178484962, compound

Product 1

HCID 20439386HCID 20439386, compoundYield 0.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-Amino-N'-methyl-N"-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]guanidine hydroiodide (2.24 g) and glycolic acid (1.52 g) were heated together for 3 h in dry benzene (25 ml) at reflux. The benzene was decanted from the residual oil, which was partitioned between ethyl acetate and aqueous 1N sodium hydroxide solution. The organic phase was chromatographed on silica using methanol to give a white solid. This solid was washed with boiling ethyl acetate to leave the title compound as a white solid (0.013 g) m.p. 151°-2°.

Workup

  1. temperatureat reflux
  2. customThe benzene was decanted from the residual oil, which
  3. customwas partitioned between ethyl acetate and aqueous 1N sodium hydroxide solution
  4. customThe organic phase was chromatographed on silica
  5. customto give a white solid
  6. washThis solid was washed with boiling ethyl acetate

Sources & evidence

ORD record
ord-925bfb0cf0f04e77b078278809814672
Source dataset
uspto-grants-1984_11
Patent number
US04481199

Reaction notes

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