Ammonia → HCID 9991164, compound

HRID 1956586Notes

Reaction equation

HRID 1956586 reaction equation
Br[CH2:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[NH3:18]>C1(C)C=CC=CC=1>[CH:17]1[C:5]2[CH:4]=[C:3]([CH2:2][NH2:18])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18663590HCID 18663590, compound

Product 1

HCID 9991164HCID 9991164, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.0 g (3.48 mmol) of 10-bromomethyl-dibenz[b,f]oxepine in 3 ml of toluene is added dropwise at 40° C. to 30 ml of NH3 -saturated methanol and the mixture is stirred at 35°-50° C. for 1 hour and at room temperature overnight. The solvent is partially removed, and the reaction mixture is taken up in tert-butyl methyl ether, washed with 0.1N sodium hydroxide solution and extracted with 1N hydrochloric acid. The aqueous phase is rendered basic with sodium hydroxide pellets and extracted with tert-butyl methyl ether, the organic phase is dried over sodium sulfate and the solvent is removed. 349 mg (1.56 mmol)=45% of N-(dibenz[b,f]oxepin-10-ylmethyl)amine are obtained in the form of a light-yellow oil; TLC (silica gel; ethyl acetate; UV): Rf =0.09.

Workup

  1. customThe solvent is partially removed
  2. washwashed with 0.1N sodium hydroxide solution
  3. extractionextracted with 1N hydrochloric acid
  4. extractionextracted with tert-butyl methyl ether
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-d4527d244812410a8f34822a2b97a8b9
Source dataset
uspto-grants-1998_07
Patent number
US05780501

Reaction notes

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