Ammonium Chloride → 10-Hydroxy-10-(3-methoxy-2-methylpropyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole

HRID 2231821노트

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HRID 2231821 반응식
Br[CH2:2][CH:3]([CH3:7])[CH2:4][O:5][CH3:6].[Mg].[N:9]1[CH2:10][CH2:11][CH2:12][N:13]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15](=[O:22])[C:14]=12.[Cl-].[NH4+]>CCOCC.ClCCCl>[OH:22][C:15]1([CH2:2][CH:3]([CH3:7])[CH2:4][O:5][CH3:6])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[N:13]2[CH2:12][CH2:11][CH2:10][N:9]=[C:14]12

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 141813833,4-Dihydropyrimido(1,2-a)indol-10(2h)-oneHCID 212848141-Bromo-3-methoxy-2-methylpropane

생성물 1

HCID 1418140110-Hydroxy-10-(3-methoxy-2-methylpropyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 3283Diethyl Ether용매2회

실험 절차

1-Bromo-3-methoxy-2-methylpropane (10.02 g) in ether (50 ml) was added dropwise over 20 minutes to magnesium turnings (1.46 g) in ether (10 ml). The mixture was stirred under argon at room temperature for 30 minutes, cooled to 0° and 3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (3.72 g) in dry 1,2-dichloroethane (20 ml) added dropwise over 20 minutes. The solution was stirred under argon at 0° for 1 hour, poured onto a swirling mixture of ice (100 ml) and saturated aqueous ammonium chloride (60 ml). The mixture was stirred for 20 minutes and concentrated in vacuo. The aqueous residue was extracted with chloroform (3×100 ml). The extracts were dried (Na2SO4) and concentrated in vacuo. Ether (20 ml) was added and the product was filtered and recrystallised from ethyl acetate to give the title compound as the free base (2.85 g), m.p. 162°-167° C. The free base was acidified with ethereal HCl to give the title compound as the hydrochloride, m.p. 244° (dec.).

후처리

  1. temperaturecooled to 0°
  2. stirringThe solution was stirred under argon at 0° for 1 hour
  3. stirringThe mixture was stirred for 20 minutes
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous residue was extracted with chloroform (3×100 ml)
  6. dry with materialThe extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. additionEther (20 ml) was added
  9. filtrationthe product was filtered
  10. customrecrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-b7217d2fe0cb451b86ef71bc27825076
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04784996

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