Potassium Carbonate → (S)-N-(2,3-dihydrofuro[3,2-f]-1,4-benzodioxin-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine monofumarate monohydrate

HRID 275781

반응식

HRID 275781 반응식
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(#N)C.C(O)C>[OH2:2].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[O:28]1[C:26]2[C:25]3[CH:24]=[CH:23][O:30][C:10]=3[CH:9]=[CH:14][C:1]=2[O:4][CH2:11][C@@H:12]1[CH2:13][NH:22][CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])[CH2:16][CH2:17]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 10608971(1-(2-Methoxyphenyl)piperidin-4-yl)methanamine

생성물 1

HCID 22951199(S)-N-(2,3-dihydrofuro[3,2-f]-1,4-benzodioxin-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine monofumarate monohydrate수율 187%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 6342Acetonitrile용매

실험 절차

A mixture of the product from the previous reaction (2.80 g), potassium carbonate (10.0 g) and 1-[(2-methoxyphenyl)piperid-4-yl]methylamine (1.88 g) in dry acetonitrile (100 ml) was heated under reflux with stirring for 90 hours. The cooled mixture was filtered and the filtrate evaporated under reduced pressure to leave a pale-yellow oil. Purification by flash column chromatography on silica eluting with a 19:1 mixture of dichloromethane and methanol gave a pale-yellow oil which was then dissolved in ethanol (5 ml) and treated with a solution of fumaric acid (0.70 g) in ethanol (5 ml). The solvent was evaporated from the resulting solution under reduced pressure to give (S)-N-(2,3-dihydrofuro[3,2-f]-1,4-benzodioxin-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine monofumarate monohydrate (3.06 g) as a pale-yellow solid m.p. 95-6° C., [α]D =−38.5° (C=0.301, MeOH).

후처리

  1. additionA mixture of the product
  2. temperaturewas heated
  3. temperatureunder reflux
  4. filtrationThe cooled mixture was filtered
  5. customthe filtrate evaporated under reduced pressure
  6. customto leave a pale-yellow oil
  7. customPurification by flash column chromatography on silica eluting
  8. additionwith a 19:1 mixture of dichloromethane and methanol
  9. customgave a pale-yellow oil which
  10. customThe solvent was evaporated from the resulting solution under reduced pressure

출처 및 근거

ORD 기록
ord-bb2a303317954c228bf43deb7b1dede9
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353002B2

연결된 노트

불러오는 중…