Acetone Cyanohydrin → 4-(3-methyl-piperidino)-tetrahydro-4H-thiopyran-4-carbonitrile

HRID 1251365ノート

反応式

HRID 1251365 の反応式
S([O-])([O-])(=O)=O.[Mg+2].[CH3:7][C:8]([N:10](C)C)=O.[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.[S:20]1[CH2:25][CH2:24]C(=O)[CH2:22][CH2:21]1.CC(C)(O)C#N.N(ON)=O>CC(C)=O>[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:7]2([C:8]#[N:10])[CH2:24][CH2:25][S:20][CH2:21][CH2:22]2)[CH2:15]1

参加物

8

反応物 6

HCID 6406Acetone CyanohydrinHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31374DimethylacetamideHCID 66173Tetrahydrothiopyran-4-one2 回HCID 790813-MethylpiperidineHCID 21703181Amino nitrite

生成物 1

HCID 183239454-(3-methyl-piperidino)-tetrahydro-4H-thiopyran-4-carbonitrile

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
45 °C

実験手順

Magnesium sulphate (9.6 g, 80 mmoles), DMA (2 g, 23 mmoles), (±)-3-methylpiperidine (4 g, 40 mmoles), tetrahydro-4H-thiopyran-4-one (2.3 g, 20 mmoles) and acetone cyanohydrin (1.7 g, 20 mmoles) are introduced in succession into a 250 ml two-necked flask. The reaction medium is agitated for 48 hours at 45° C. After cooling down to ambient temperature, the pasty mixture obtained is placed on ice (approximately 150) and agitated for 30 minutes. Extraction with ether is then carried out (3×80 ml), the combined organic phases are washed with water (100 ml), followed by drying over Na2SO4, filtering and concentration to dryness. A brown oil is thus obtained (4.5 g, 20 mmoles) constituted by a mixture of expected product with approximately 4% of amino nitrite originating from acetone and 7% of the remaining tetrahydro-4H-thiopyran-4-one. The product is then used without further purification.

後処理

  1. temperatureAfter cooling down to ambient temperature
  2. customthe pasty mixture obtained
  3. stirringagitated for 30 minutes
  4. extractionExtraction with ether
  5. washthe combined organic phases are washed with water (100 ml)
  6. dry with materialby drying over Na2SO4
  7. filtrationfiltering
  8. concentrationconcentration to dryness
  9. customA brown oil is thus obtained (4.5 g, 20 mmoles)

出典と根拠

ORDレコード
ord-5bd7d50a09be47ba8580f26c5ee364d3
出典データセット
uspto-grants-2002_01
特許番号
US06342511B1

反応ノート

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