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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
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HRID 463311 반응식
[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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bea82bf36232476a840a072b76318466
출처 데이터셋
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04518713

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