Water → 2,3-Bis(piperidinomethyl)naphthalene dihydrochloride

HRID 461448ノート

反応式

HRID 461448 の反応式
[N:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[Cl:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>CCOCC>[ClH:23].[ClH:23].[N:1]1([CH2:7][C:8]2[C:17]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 962WaterHCID 204543Piperidine, 1-(2-naphthalenylmethyl)-HCID 11974404N-chloromethylpiperidineHCID 178418339Butyllithium

生成物 1

HCID 213937412,3-Bis(piperidinomethyl)naphthalene dihydrochloride

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a stirred solution of 2-piperidinomethylnaphthalene (5.6 g) in dry ether (200 ml) was added, under nitrogen, a 1.5M ethereal solution of butyl lithium (18.3 ml) and the mixture was kept at room temperature for 24 hours. N-(Chloromethyl)piperidine (7.34 g) was added, the mixture was heated under reflux for 1 hour, and poured into water (1 l). The precipitated material was extracted into ether, the extract was washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was purified by chromatography on silica and an ethereal solution of the product was treated with ethereal hydrogen chloride. 1,2-Bis(piperidinomethyl)naphthalene dihydrochloride crystallised from propan-2-ol as prisms, m.p. 240°.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionThe precipitated material was extracted into ether
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on silica
  8. additionan ethereal solution of the product was treated with ethereal hydrogen chloride
  9. custom1,2-Bis(piperidinomethyl)naphthalene dihydrochloride crystallised from propan-2-ol as prisms, m.p. 240°

出典と根拠

ORDレコード
ord-4150f064f5894e67a7a8a6d4a73e9703
出典データセット
uspto-grants-1977_12
特許番号
US04062955

反応ノート

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