Formaldehyde → HCID 19044758, compound

HRID 1682553Notes

Reaction equation

HRID 1682553 reaction equation
[CH2:1]=[O:2].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][C:22]2[C:27]([CH2:28][OH:29])=[C:26]([OH:30])[CH:25]=[CH:24][C:23]=2[CH2:31]O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)Cl>[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:21][CH:22]([C:23]3[CH:24]=[CH:25][C:26]([OH:30])=[C:27]([CH2:28][OH:29])[CH:31]=3)[O:2][CH2:1]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 19044759HCID 19044759, compound

Product 1

HCID 19044758HCID 19044758, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With stirring, 0.18 ml 36.5% aqueous formaldehyde are added at room temperature to a suspension of 0.589 g of (RS)-α1 -[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-4-hydroxy-1,3-dihydroxymethylbenzene (racemic mixture of R- and S-enantiomers) in 14 ml of methylene chloride. The mixture is stirred for 1 hour, diluted with methylene chloride and stirred for 14 hours at room temperature. The solution is washed with water (2×10 ml), dried over magnesium sulfate and concentrated by evaporation at 20 mbar and 30° C. The residue is dried at 0.1 mbar at 30° C. for 4 hours, giving the racemate of (SR)-3-[6-(4-phenylbutoxy)hexyl]-5-(4-hydroxy-3-hydroxymethylphenyl)oxazolidine in the form of a crystalline powder; m.p. 72°-75° C. [1H-NMR (400 MHZ, CD2Cl2)]: identical with the spectrum of the compound of Example 1.

Workup

  1. stirringThe mixture is stirred for 1 hour
  2. stirringstirred for 14 hours at room temperature
  3. washThe solution is washed with water (2×10 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation at 20 mbar and 30° C
  6. customThe residue is dried at 0.1 mbar at 30° C. for 4 hours

Sources & evidence

ORD record
ord-f79873138413436eaaf5f53a95f4d6d6
Source dataset
uspto-grants-1997_06
Patent number
US05635524

Reaction notes

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