Trifluoroacetic acid → 5-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[perhydro-azepine-3,3'-piperidine]

HRID 83980

反応式

HRID 83980 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:17][CH2:16][CH2:15]/[C:14](=[CH:18]/OC)/[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[ClH:21].ClC1C=C[C:26]([NH:29]N)=CC=1.F[C:32](F)(F)[C:33](O)=O.C([SiH](CC)CC)C.[OH-].[NH4+]>C(Cl)(Cl)Cl.ClCCl>[Cl:21][CH:33]1[CH2:32][CH2:26][NH:29][CH2:13][C:14]2([CH2:15][CH2:16][CH2:17][N:11]([CH2:10]/[CH:9]=[CH:8]/[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12]2)[CH2:18]1

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14923Ammonium HydroxideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 68924237[(e)-3-(4-Chloro-phenyl)-allyl]-4-[1-methoxy-meth-(z)-ylidene]-perhydro-azepine

生成物 1

HCID 689278545-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[perhydro-azepine-3,3'-piperidine]

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of -[(E)-3-(4-Chloro-phenyl)-allyl]-4-[1-methoxy-meth-(Z)-ylidene]-perhydro-azepine (0.6 g) and 4-chlorophenylhydrazine hydrochloride (0.41 g) in chloroform (20 ml) was treated with trifluoroacetic acid (2.1 ml) and heated at reflux under argon for 18 hours. The reaction mixture was cooled to room temperature, triethylsilane (3.1 ml) was added and the solution refluxed for 2 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane, neutralised with 30% aqueous ammonium hydroxide, washed with brine, dried (sodium sulphate) and concentrated. The dark residue was purified by silica gel chromatography (cyclohexane:ethyl acetate 1:9) to afford 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[perhydro-azepine-3,3′-piperidine] (529 mg). MS (ES+) 387/389 (M+H′).

後処理

  1. temperatureheated
  2. temperatureat reflux under argon for 18 hours
  3. temperaturethe solution refluxed for 2 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed with brine
  6. dry with materialdried (sodium sulphate)
  7. concentrationconcentrated
  8. customThe dark residue was purified by silica gel chromatography (cyclohexane:ethyl acetate 1:9)

出典と根拠

ORDレコード
ord-5ea29847c5bb4082a666dc9a4d12ab29
出典データセット
uspto-grants-2014_09
特許番号
US08846907B2

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