Formaldehyde → HCID 86637498, compound

HRID 1676512Notes

Reaction equation

HRID 1676512 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[C:10]1([C@@H:16]2[CH2:18][C@H:17]2[NH2:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:20]=O>CCOCC>[N:1]1([CH2:20][NH:19][C@@H:17]2[CH2:18][C@H:16]2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 19493(1R,2S)-TranylcypromineHCID 178418385HCID 178418385, compound

Product 1

HCID 86637498HCID 86637498, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the mixture of 6.7 g (0.056 mole) benzotriazole and 7.4 g (0.056 mole) of trans-2-phenyl-cyclopropylamine in 150 mL of ether was added dropwise 4.5 mL (0.056 mole) of 37% aqueous formaldehyde. The reaction mixture was stirred at room temperature overnight. The solution was dried over calcium chloride, filtered and concentrated under pressure. Hexane was added under ice-cooled bath and the resulting solid was collected by filtration and washed with hexane dried to give 15 g of benzotriazol-1-ylmethyl-(trans-2-phenyl-cyclopropyl)-amine as an oil.

Workup

  1. dry with materialThe solution was dried over calcium chloride
  2. filtrationfiltered
  3. concentrationconcentrated under pressure
  4. additionHexane was added under ice-
  5. temperaturecooled bath
  6. filtrationthe resulting solid was collected by filtration
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-34f4eb69f7594da996b7356fed3c4333
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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