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 1532055ノート

反応式

HRID 1532055 の反応式
[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

参加物

6

反応物 3

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

生成物 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 monohydrate収率 187%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-110740fe11a748f09ae454e8cbe6540c
出典データセット
uspto-grants-2001_03
特許番号
US06201004B1

反応ノート

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