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Sodium Hydroxide → 1-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-phenoxypiperidine dihydrochloride

HRID 463311
ノート
印刷プレビュー

反応式

HRID 463311 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][CH:30]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:29][CH2:28]3)=O)[CH3:23])[O:18][CH2:17][CH2:16][O:15]2)=[CH:10][CH:9]=1.[OH-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:54].Cl>C1COCC1.O>[ClH:54].[ClH:54].[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][N:27]3[CH2:28][CH2:29][CH:30]([O:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH2:31][CH2:32]3)[CH3:23])[O:15][CH2:16][CH2:17][O:18]2)=[CH:12][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 202831171-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-phenoxypiperidineHCID 21226445Aluminium lithium hydride

生成物 1

HCID 202830621-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-phenoxypiperidine dihydrochloride

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 1.9 g (25.1 mmol) of lithium aluminum hydride (50% in oil; washed three times with hexane) in 75 ml dry THF, cooled by an ice bath, was added dropwise a solution of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-phenoxypiperidine (from above) in 75 ml of dry THF. The suspension was heated at reflux for 12 hours and allowed to cool to room temperature. To the mixture, in an ice bath were added slowly dropwise 1 ml of water, 1 ml of 15% NaOH and 3 ml of water. The mixture was filtered and washed with THF. The solvent was evaporated from the filtrate to provide an oil which was extracted with ether and washed with saturated sodium chloride. The solution was dried over potassium carbonate and filtered to provide an oil. The overall yield of the dihydrochloride was 7.47 g (82.0%).

後処理

  1. temperaturecooled by an ice bath
  2. temperatureThe suspension was heated
  3. temperatureat reflux for 12 hours
  4. filtrationThe mixture was filtered
  5. washwashed with THF
  6. customThe solvent was evaporated from the filtrate
  7. customto provide an oil which
  8. extractionwas extracted with ether
  9. washwashed with saturated sodium chloride
  10. dry with materialThe solution was dried over potassium carbonate
  11. filtrationfiltered
  12. customto provide an oil

出典と根拠

ORDレコード
ord-bea82bf36232476a840a072b76318466
出典データセット
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04518713

反応ノート

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