Formic Acid → HCID 22405626, compound

HRID 440834Notes

Reaction equation

HRID 440834 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.C=[O:20].[CH:21]([OH:23])=[O:22]>>[C:12]([OH:20])(=[O:11])/[CH:13]=[CH:14]/[C:21]([OH:23])=[O:22].[CH3:21][N:15]1[CH2:16][CH2:17][O:18][CH:13]([CH2:12][O:11][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[C:10]3[C:6]=2[CH2:7][CH2:8][CH2:9]3)[CH2:14]1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 15342071161178-07-0

Product 1

HCID 22405626HCID 22405626, compound

Conditions

Temperature
80 °C

Procedure

To 180 mg of 2-[[(7-fluoro-4-indanyl)oxy]methyl]morpholine were added 1 ml of a 35% aqueous formaldehyde solution and 1 ml of formic acid, and the mixture was stirred at 80° C. for 7 hours, followed by concentration under reduced pressure. The concentrate was neutralized by addition of 20 ml of a saturated aqueous solution of sodium hydrogencarbonate. The mixture was extracted with three 20 ml portions of ethyl ether. The ethyl ether solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oil was dissolved in 20 ml of ethyl ether, and a solution of 42 mg of fumaric acid in 1 ml of methanol was added thereto while stirring. The precipitated salt was collected by filtration, washed with ethyl ether, and dried to give 123 mg of 4-methyl-2-[[(7-fluoro-4-indanyl)oxy]methyl]morpholine fumarate.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. additionThe concentrate was neutralized by addition of 20 ml of a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionThe mixture was extracted with three 20 ml portions of ethyl ether
  4. dry with materialThe ethyl ether solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting oil was dissolved in 20 ml of ethyl ether
  7. additiona solution of 42 mg of fumaric acid in 1 ml of methanol was added
  8. stirringwhile stirring
  9. filtrationThe precipitated salt was collected by filtration
  10. washwashed with ethyl ether
  11. customdried

Sources & evidence

ORD record
ord-c919285c858047b4b374e0fae0578adf
Source dataset
uspto-grants-1996_05
Patent number
US05521180

Reaction notes

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