Sodium Iodide → 1-[3-(Diphenylamino)propyl]-alpha-penyl-4-piperidine methanol

HRID 1578310ノート

反応式

HRID 1578310 の反応式
[C:1]1([N:7]([CH2:14][CH2:15][CH2:16]Cl)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([CH:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[OH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CCOCC.C1(C)C=CC=CC=1>[C:1]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][CH2:16][N:29]2[CH2:28][CH2:27][CH:26]([CH:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[OH:25])[CH2:31][CH2:30]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 339086Phenyl-piperidin-4-yl-methanolHCID 106580533-(N,N-diphenylamino)-1-chloropropane

生成物 1

HCID 127638861-[3-(Diphenylamino)propyl]-alpha-penyl-4-piperidine methanol収率 16.6%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 9.8 g. (0.040 moles) of 3-[N,N-diphenylamino]-1-chloropropane, 5.7 g. (0.030 moles) of alpha-phenyl-4-piperidine methanol (preparation described in U.S. Pat. No. 3,029,244 to Lyle, Jr. et al, issued Apr. 10, 1962), 4.2 g. (0.040 moles) of sodium carbonate and 0.5 g. of sodium iodide in 90 ml. of toluene is refluxed for about 18 hours. The reaction mixture is cooled, washed with water, and then shaken with dilute hydrochloric acid. The viscous third layer which falls to the bottom is isolated and shaken with ether and dilute caustic. The resulting ether layer is then washed with water, dried, and passed into a column of silica gel. The product is eluted with ethyl acetate and the product fractions are combined, evaporated, and triturated with isopropyl ether. The resulting crystals are isolated by filtration and recrystallized from ethanol to give 2.0 g of 1-[3-(diphenylamino)propyl]-alpha-penyl-4-piperidine methanol, mp. 129.0°-130.5° C. 1-[3-(Diphenylamino)propyl]-alpha-phenyl-4-piperidine methanol shows approximately no inhibition of 3H-haloperidol binding at 10 n moles concentration and approximately 18% inhibition of hu 3H-haloperidol binding at 100 n moles concentration in the 3H-Haloperidol Receptor Binding Assay.

後処理

  1. additionA mixture of 9.8 g
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water
  4. custombottom is isolated
  5. additiondilute caustic
  6. washThe resulting ether layer is then washed with water
  7. customdried
  8. washThe product is eluted with ethyl acetate
  9. customevaporated
  10. customtriturated with isopropyl ether
  11. customThe resulting crystals are isolated by filtration
  12. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-d89ecdd2c16e492eb8658dbeefdb6a73
出典データセット
uspto-grants-1981_09
特許番号
US04292321

反応ノート

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