Phenylacetonitrile → 1-Tert-butyl-4-phenylpiperidine-4-carbonitrile

HRID 1800821

反応式

HRID 1800821 の反応式
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:13][CH2:14][N:15]([CH2:20][CH2:21]Cl)[C:16]([CH3:19])([CH3:18])[CH3:17]>CS(C)=O.Cl>[C:16]([N:15]1[CH2:20][CH2:21][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:8]#[N:9])[CH2:13][CH2:14]1)([CH3:19])([CH3:18])[CH3:17]

参加物

6

反応物 3

HCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 96167Triethylamine, 2',2''-dichloro-1,1-dimethyl-

生成物 1

HCID 130468591-Tert-butyl-4-phenylpiperidine-4-carbonitrile収率 68%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
23 °C

実験手順

A solution of phenyl acetonitrile (1.0 g, 8.54 mmol) in DMSO (8 mL) was treated with sodium hydride (0.717 g, 29.88 mmol) portionwise. The resulting-suspension was stirred at 23° C. for 30 minutes. N,N-bis(2-chloroethyl)-2-methylpropan-2-amine (2.20 g, 9.39 mmol) was then slowly added over 5 minutes, then the suspension was heated at 65° C. overnight. The reaction was then diluted with 1N hydrochloric acid and washed with ethyl acetate (2×). The aqueous phase was basified with sat. aq. sodium carbonate and extracted with ethyl acetate (3×). The combined extracts were washed with water (5×), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil (1.40 g, 68%) which solidified on standing and was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 2.10-2.17 (3H, m), 2.31-2.37 (1H, m), 2.42 (3H, s), 2.47-2.57 (2H, m), 3.01 (2G, d, J=12.6 Hz), 7.45 (2H, dd, J=4.55 and 1.52 Hz), 8.68 (2H, dd, J=4.55 and 1.77 Hz).

後処理

  1. temperaturethe suspension was heated at 65° C. overnight
  2. washwashed with ethyl acetate (2×)
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined extracts were washed with water (5×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fbd69499da744215af03b08e7a414372
出典データセット
uspto-grants-2013_01
特許番号
US08343999B2

関連ノート

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