Trisodium Phosphate → (3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine

HRID 1729124

반응식

HRID 1729124 반응식
[CH3:1][NH:2][CH2:3][CH2:4]/[CH:5]=[C:6]1\[C:7]2[C:12]([CH2:13][O:14][C:15]3[C:20]\1=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=[CH:9][CH:8]=2.P([O-])([O-])([O-])=[O:22].[Na+].[Na+].[Na+]>C1COCC1.[Zn]>[CH2:20]1[CH2:15][O:14][CH2:18][CH2:19]1.[CH3:13][OH:14].[NH4+:2].[OH-:22].[CH3:1][NH:2][CH2:3][CH2:4]/[CH:5]=[C:6]1\[C:7]2[C:12]([CH2:13][O:14][C:15]3[C:20]\1=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=[CH:9][CH:8]=2

참가 물질

6

반응물 2

HCID 24243Trisodium PhosphateHCID 6433351(3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine

생성물 2

HCID 6433351(3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamineHCID 86686122THF MeOH NH4OH

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

실험 절차

The N-protected (E)-desmethyldoxepin intermediate (1.44 g, 3.27 mmol) was dissolved in 12 mL THF, 2.88 g of zinc powder added, 2.3 mL of 1M sodium phosphate (pH=5.5) added, and reaction stirred for 17 hours. The reaction mixture was then vacuum filtered, filtrate solvent removed in vacuo, and resulting residue purified by silica gel column chromatography, eluting with THF/MeOH/NH4OH (85/15/0.4), then THF/MeOH/NH4OH (75/25/0.4), to afford 744 mg (2.80 mmol) of the desired product [3] as a pale yellow solid; 1H NMR (200 MHz, CDCl3): d 2.5 (s, 3H), 2.7 (m, 2H), 3.0 (m, 2H), 4.7-5.8 (broad s, 2H), 6.0 (t, 1H), 6.8-6.9 (m, 2H), 7.1-7.4 (m, 6H); mass spec (FAB): (M+H)+266.

후처리

  1. customreaction
  2. filtrationvacuum filtered
  3. customfiltrate solvent removed in vacuo
  4. customresulting residue
  5. custompurified by silica gel column chromatography
  6. washeluting with THF/MeOH/NH4OH (85/15/0.4)

출처 및 근거

ORD 기록
ord-fb20430bebd94c4096165067143b32bf
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05332661

연결된 노트

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