Water → 1-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

HRID 463309ノート

反応式

HRID 463309 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C(O)=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([CH2:25][CH2:26][CH2:27][N:28]([CH2:30][C:31]([N:33]3[CH2:38][CH2:37][CH:36]([O:39][C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=4)[CH2:35][CH2:34]3)=O)[CH3:29])[O:24][CH2:23][CH2:22][O:21]2)=[CH:16][CH:15]=1.O.[OH-].[Na+]>C1COCC1>[ClH:46].[ClH:46].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([CH2:25][CH2:26][CH2:27][N:28]([CH2:30][CH2:31][N:33]3[CH2:38][CH2:37][CH:36]([O:39][C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=4)[CH2:35][CH2:34]3)[CH3:29])[O:21][CH2:22][CH2:23][O:24]2)=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 202831291-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 202830781-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylamino}ethyl}-4-(3-chlorophenoxy)piperidine dihydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension prepared from 3.00 g (39.5 mmol) of 50% lithium aluminum hydride in oil and 100 ml of dry THF and maintained at 0° was added dropwise a solution of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-(3-chlorophenoxy)piperidine oxalate in 100 ml of dry THF. The mixture was heated at reflux under nitrogen for 12 hours, allowed to cool to room temperature and subsequently cooled in an ice bath. To the mixture was added slowly, dropwise 3 ml of water followed by 3 ml of 15% sodium hydroxide and 9 ml of water. The suspension was filtered and washed with 150 ml of THF, and the THF was evaporated. The residue was extracted with ether, washed with saturated sodium chloride and dried over potassium carbonate. The yield of the dihydrochloride was 9.36 g (79%). Crystallization from ethanol provided analytically pure material.

後処理

  1. temperaturemaintained at 0°
  2. temperatureThe mixture was heated
  3. temperatureat reflux under nitrogen for 12 hours
  4. temperaturesubsequently cooled in an ice bath
  5. additionTo the mixture was added slowly
  6. filtrationThe suspension was filtered
  7. washwashed with 150 ml of THF
  8. customthe THF was evaporated
  9. extractionThe residue was extracted with ether
  10. washwashed with saturated sodium chloride
  11. dry with materialdried over potassium carbonate
  12. customCrystallization from ethanol
  13. customprovided analytically pure material

出典と根拠

ORDレコード
ord-361e5f99906a455797087e9713d04901
出典データセット
uspto-grants-1985_05
特許番号
US04518713

反応ノート

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