Formaldehyde → HCID 19600068, compound

HRID 611217Notes

Reaction equation

HRID 611217 reaction equation
C(O[C:6]([N:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:16]=[CH:15][O:14][CH:13]=1)=O)(C)(C)C.C=O>C(O)(=O)C>[C:23]1([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:8]2[CH2:9][CH2:10][CH2:11][C:12]3[CH:16]=[CH:15][O:14][C:13]=3[CH2:6]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 19600203HCID 19600203, compound

Product 1

HCID 19600068HCID 19600068, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the above crude N-[3-(3-furyl)propyl]-6-phenylhexylamine in 100 ml of acetic acid, 0.74 g (9.1 mmol) of 37% aqueous formaldehyde was added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1)

Sources & evidence

ORD record
ord-78f390fdd6754aaa82d6dc2a943939a5
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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