Formic Acid → HCID 9798574, compound

HRID 1079106Notes

Reaction equation

HRID 1079106 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[CH2:11][NH:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[CH:4][CH:3]=1.Cl.[CH:23](O)=O>C=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[CH2:11][N:12]([CH2:13][CH:14]2[CH2:16][CH2:15]2)[CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 15341894HCID 15341894, compound

Product 1

HCID 9798574HCID 9798574, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

In a mixture of 150 ml of formic acid and 150 ml of 37% formaldehyde was dissolved 80 g of 3-(4-chlorobenzyloxy)-N-cyclopropylmethylbenzylamine. The solution was refluxed with heating, for 3 hours. The reaction mixture was cooled to room temperature, and 150 ml of concentrated hydrochloric acid was added thereto. The mixture was subjected to vacuum distillation to remove the solvent. The resulting residue was treated with chloroform-aqueous sodium hydroxide solution. The resulting chloroform layer was separated, washed with water, dried with anhydrous sodium sulfate, and subjected to vacuum distillation to remove the solvent, whereby 86 g of 3-(4-chlorobenzyloxy)-N-cyclopropylmethyl-N-methylbenzylamine was obtained as a brown oil.

Workup

  1. temperatureThe solution was refluxed
  2. temperaturewith heating, for 3 hours
  3. distillationThe mixture was subjected to vacuum distillation
  4. customto remove the solvent
  5. additionThe resulting residue was treated with chloroform-aqueous sodium hydroxide solution
  6. customThe resulting chloroform layer was separated
  7. washwashed with water
  8. dry with materialdried with anhydrous sodium sulfate
  9. distillationsubjected to vacuum distillation
  10. customto remove the solvent

Sources & evidence

ORD record
ord-cbc7cacefebd44a2b9d232c3637fd9b4
Source dataset
uspto-grants-1996_08
Patent number
US05550292

Reaction notes

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