Hydrochloric Acid → HCID 18663626, compound

HRID 1956560Notes

Reaction equation

HRID 1956560 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.[CH2:18]([NH2:21])[CH:19]=[CH2:20].COC(C)(C)C.[ClH:28]>CO.C(OCC)C.C(OCC)(=O)C>[ClH:28].[CH2:18]([NH:21][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)[CH:19]=[CH2:20].[CH2:18]([NH:21][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)[CH:19]=[CH2:20]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 15413tert-Butyl methyl etherHCID 18663590HCID 18663590, compound

Product 2

HCID 10061310HCID 10061310, compoundHCID 18663626HCID 18663626, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 50° C. a solution of 0.5 ml (1.74 mmol) of 10-bromomethyl-dibenz[b,F]oxepine is squirted into a solution of 0.3 ml (4 mmol) of allylamine in 0.9 ml of anhydrous methanol and the mixture is stirred for 30 minutes. Tert-butyl methyl ether and ethyl acetate are added and the mixture is extracted 3× with 20 ml of 1N hydrochloric acid each time, the combined aqueous phases are rendered basic with potassium hydroxide pellets and extracted 2× with ethyl acetate, and the organic phases are dried over sodium sulfate and concentrated. 0.35 ml (0.7 mmol) of 2N ethereal hydrochloric acid is added to the crude amine (180 mg) in 2 ml of diethyl ether, and the precipitated white hydrochloride is washed with diethyl ether and dried under a high vacuum at 40° C. 200 mg (667 μmol)=39% of the title compound alias 10-allylaminomethyl-dibenz[b,f]oxepine are obtained in the form of white crystals; melting point: 148°-158° C.; 1H-NMr (CD3OD, 200 MHz). 3.74 (d, 2H); 4.35 (d, 2H), 5.55 (m, 2H); 5.95 (m, 1H); 7.20-7.58 (m, 9H); MS: 263 (M+, free base), 222, 208, 181, 165, 152.

Workup

  1. customAt 50° C.
  2. extractionthe mixture is extracted 3× with 20 ml of 1N hydrochloric acid each time
  3. extractionextracted 2× with ethyl acetate
  4. dry with materialthe organic phases are dried over sodium sulfate
  5. concentrationconcentrated
  6. washthe precipitated white hydrochloride is washed with diethyl ether
  7. customdried under a high vacuum at 40° C

Sources & evidence

ORD record
ord-936fc637f31144c18c097e4bdb7c27b5
Source dataset
uspto-grants-1998_07
Patent number
US05780500

Reaction notes

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