Water → Omigapil

HRID 1956559Notes

Reaction equation

HRID 1956559 reaction equation
[CH3:1][NH:2][CH2:3][C:4]#[CH:5].Br[CH2:7][C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][C:11]2[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=2[CH:9]=1.O>C1C=CC=CC=1.CO>[CH:22]1[C:10]2[CH:9]=[C:8]([CH2:7][N:2]([CH3:1])[CH2:3][C:4]#[CH:5])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 96160N-methylpropyn-2-ylamineHCID 18663590HCID 18663590, compound

Product 1

HCID 6419718OmigapilYield 77%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent

Procedure

Methylpropargylamine (4.5 g, 65 mmol) is dissolved in benzene (75 ml) and methanol (25 ml). At 40° C. a solution of 10-bromomethyldibenz[b,f]oxepine (7.0 g, 25 mmol) in benzene (25 ml) is added dropwise in the course of half an hour. When the addition is complete, the mixture is stirred for a further half hour at 40°-50° C., poured into water, washed three times with water and then extracted with 5% methanesulfonic acid. The acidic aqueous phase is rendered basic with concentrated ammonia and extracted with diethyl ether. The ethereal phase is dried over sodium sulfate and concentrated by evaporation. Crystallisation of the residue from petroleum ether yields N-(dibenz[b,f]oxepin-10-ylmethyl-N-methyl-N-prop-2-ynylamine alias 10-(N-propargyl-N-methyl-amino)methyldibenz[b,f]oxepine (5.3 g, 77%). Melting point: 66°-67° C.

Workup

  1. additionWhen the addition
  2. washwashed three times with water
  3. extractionextracted with 5% methanesulfonic acid
  4. extractionextracted with diethyl ether
  5. dry with materialThe ethereal phase is dried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customCrystallisation of the residue from petroleum ether

Sources & evidence

ORD record
ord-c6c3b9c21b484a68871215b1e6767dd4
Source dataset
uspto-grants-1998_07
Patent number
US05780500

Reaction notes

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