Formic Acid → HCID 178458332, compound

HRID 979896Notes

Reaction equation

HRID 979896 reaction equation
[CH2:1]([O:4][C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[O:7][CH2:8][CH:9]([OH:24])[CH2:10][NH:11][C@@H:12]1[CH2:17][CH2:16][C@H:15]([N:18]2[CH2:22][CH2:21][NH:20][C:19]2=[O:23])[CH2:14][CH2:13]1)[CH:2]=[CH2:3].C=O.[CH:31](O)=O.Cl>C(O)(C)C>[CH2:1]([O:4][C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[O:7][CH2:8][CH:9]([OH:24])[CH2:10][N:11]([C@@H:12]1[CH2:17][CH2:16][C@H:15]([N:18]2[CH2:22][CH2:21][NH:20][C:19]2=[O:23])[CH2:14][CH2:13]1)[CH3:31])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 178458333HCID 178458333, compound

Product 1

HCID 178458332HCID 178458332, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of cis-1-(4-[3-(o-allyloxyphenoxy)-2-hydroxypropylamino]-cyclohexyl)-2-imidazolidinone (4.4 g) in 15 ml isopropanol, 37.5% aqueous formaldehyde (0.671 g), and formic acid (2.6 g) is stirred at reflux for 19 hours. The solution is cooled to room temperature, 1 ml concentrated hydrochloric acid is added and the mixture concentrated to dryness. The glassy residue is dissolved in 100 ml of water, made alkaline with excess of 25% aqueous sodium hydroxide and extracted with methylene chloride (1×50 ml, 1×25 ml). The extract is dried, filtered and concentrated to give a residue which is purified by preparative thin layer chromatography on silica gel, using ethyl acetate-methanol-ammonium hydroxide (90:5:5) as the eluent, to yield the cis-1-{4-[3-(o-allyloxyphenoxy)-2-hydroxy-N-methyl-propylamino]cyclohexyl}-2imidazolidinone as an oil. The hydrochloride salt, m.p. 80° dec., is prepared by dissolving 2.3 g of the base in 50 ml ethyl acetate, adding a saturated solution of hydrogen chloride gas in ethyl acetate, and collecting the resulting salt.

Workup

  1. temperatureat reflux for 19 hours
  2. concentrationthe mixture concentrated to dryness
  3. dissolutionThe glassy residue is dissolved in 100 ml of water
  4. extractionextracted with methylene chloride (1×50 ml, 1×25 ml)
  5. customThe extract is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue which
  9. customis purified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-0540d0196d92425f837c5d9f626c3ecf
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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