Piperidine → Spiro(cyclopentane-1,1'-indan)-3'-ylideneacetonitrile

HRID 426918

反応式

HRID 426918 の反応式
C(CC(O)=O)#N.C12(CCCC1)C1C(=CC=CC=1)C(=O)C2.N1CCCCC1.[C:27]12([CH2:42][CH2:41][CH2:40][CH2:39]1)[C:35]1[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:29]([CH2:36][C:37]#[N:38])=[CH:28]2>CCCCCC.O.C1C=CC=CC=1>[C:27]12([CH2:42][CH2:41][CH2:40][CH2:39]1)[C:35]1[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:29](=[CH:36][C:37]#[N:38])[CH2:28]2

参加物

8

反応物 4

HCID 8082PiperidineHCID 9740Cyanoacetic acidHCID 20388411Spiro(cyclopentane-1,1'-indene)-3'-ylacetonitrileHCID 203884122',3'-Dihydrospiro[cyclopentane-1,1'-inden]-3'-one

生成物 1

HCID 54124997Spiro(cyclopentane-1,1'-indan)-3'-ylideneacetonitrile

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 962Water溶媒HCID 8058Hexane溶媒

実験手順

To a mixture of cyanoacetic acid (85 g; 1.0 moles) and spiro(cyclopentane-1,1'-indan)-3'-one (186 g; 1.0 moles) there is added piperidine (85.2 g; 1.0 moles) dropwise under agitation and cooling at such a rate that the temperature does not exceed 40°-60° C. After addition of benzene (300 ml) the mixture is refluxed for 24 hours with continuous separation of the water formed. Benzene and piperidine are distilled off under reduced pressure and the oil obtained is distilled in vacuum. At 130°-140° C./1 torr there is obtained a colourless oil consisting of the title nitrile as well as the isomer spiro(cyclopentane-1,1'-indene)-3'-ylacetonitrile and a small amount of unreacted ketone. The mixture is dissolved in hot hexane and cooled, and then spiro(cyclopentane-1,1'-indan)-3'-ylideneacetonitrile crystallizes as colourless crystals of mp 82° C.

後処理

  1. temperaturecooling at such a rate that the temperature
  2. customdoes not exceed 40°-60° C
  3. customformed
  4. distillationBenzene and piperidine are distilled off under reduced pressure
  5. customthe oil obtained
  6. distillationis distilled in vacuum
  7. customAt 130°-140° C./1 torr there is obtained a colourless oil
  8. temperaturecooled
  9. customspiro(cyclopentane-1,1'-indan)-3'-ylideneacetonitrile crystallizes as colourless crystals of mp 82° C.

出典と根拠

ORDレコード
ord-b2a3901a111d4e58baca1d29d79e16b5
出典データセット
uspto-grants-1979_10
特許番号
US04172093

関連ノート

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