Benzyl Bromide → 6-[p-(Benzyloxy)phenyl]-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate

HRID 486571

반응식

HRID 486571 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH2:13][CH2:14][N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O.C(O)C.C(Cl)Cl>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]3[CH2:13][CH2:14][N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

9

반응물 4

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 1357369333,4-Dihydro-6-(4-hydroxyphenyl)-1-methylpyrrolo[1,2-a]pyrazine

생성물 1

HCID 190954396-[p-(Benzyloxy)phenyl]-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate수율 19%

시약·촉매·용매 4

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromide촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 6344Dichloromethane용매2회

실험 절차

3,4-Dihydro-6-(4-hydroxyphenyl)-1-methylpyrrolo[1,2-a]pyrazine (5.0 g), 100 ml of methylene chloride, 5.3 ml of benzyl bromide and 0.8 g of benzyltributylammonium bromide was added in succession to a solution of 1.8 g of sodium hydroxide in 100 ml of water under argon. The mixture was boiled under reflux overnight and stirred and subsequently cooled. After the addition of 100 ml of methylene chloride and 100 ml of water the phases were separated and the aqueous phase was extracted twice with 100 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 10.3 g of brown oil, was chromatographed on 500 g of silica gel with methylene chloride/methanol mixtures (99:1 to 9:1) as the eluent. The crude product, 4.9 g of brown, amorphous material, was dissolved in a 10-fold amount of hot ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. The product, 2.2 g of yellow crystals, was recrystallized from a 20-fold amount of ethanol. There were obtained 1.8 g (19%) of 6-[p-(benzyloxy)phenyl]-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 165°-168° C. (dec.).

후처리

  1. temperatureunder reflux overnight
  2. temperaturesubsequently cooled
  3. customwere separated
  4. extractionthe aqueous phase was extracted twice with 100 ml of methylene chloride each time
  5. dry with materialdried with MgSO4
  6. customThe residue, 10.3 g of brown oil, was chromatographed on 500 g of silica gel with methylene chloride/methanol mixtures (99:1 to 9:1) as the eluent
  7. dissolutionThe crude product, 4.9 g of brown, amorphous material, was dissolved in a 10-fold amount of hot ethanol
  8. customThe product, 2.2 g of yellow crystals, was recrystallized from a 20-fold amount of ethanol

출처 및 근거

ORD 기록
ord-1d37091acaeb42c99925bb1b37d2d860
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292732

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