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Methane → 6-(3-chloro-4-fluorobenzoyl)-1-Oxa-6-azaspiro[2.5]octane-2-carbonitrile

HRID 1272511
ノート
印刷プレビュー

反応式

HRID 1272511 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[C:5]([N:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1)=[O:6].Cl[CH2:19][C:20]#[N:21].C>ClCCl.[OH-].[Na+].[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[C:5]([N:7]1[CH2:8][CH2:9][C:10]2([O:13][CH:19]2[C:20]#[N:21])[CH2:11][CH2:12]1)=[O:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 297MethaneHCID 7856Chloroacetonitrile2 回HCID 10611056N-(3-chloro-4-fluorobenzoyl)-piperidine-4-one

生成物 1

HCID 120436336-(3-chloro-4-fluorobenzoyl)-1-Oxa-6-azaspiro[2.5]octane-2-carbonitrile

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒2 回
HCID 14798Sodium Hydroxide溶媒

反応条件

温度
15 °C

実験手順

A suspension of 1-(3-chloro-4-fluorobenzoyl)piperidin-4-one (4160 g, 16.27 mol) in 28.4 liters of dichloromethane and 11.7 liters of sodium hydroxide at 30.5%, supplemented with 186 g of tetrabutylammonium chloride, is cooled to 15° C. Chloroacetonitrile (1540 ml, 24.4 mol) is then added slowly and with vigorous stirring and the mixture is stirred for 3 hours at 20° C. Further addition of chloroacetonitrile (500 ml) is carried out in order to complete the reaction. The reaction medium is diluted with dichloromethane (8.5 liters) and water (20 liters) and then separated by decantation and washed again with water. The brown solution obtained is decolorized with 2 kg of silica and 500 g of animal charcoal and then evaporated to dryness. The residue obtained is crystallized from isopropanol in order to give, after filtration, 3426 g of brown crystals. m.p.=100–101° C.

後処理

  1. stirringthe mixture is stirred for 3 hours at 20° C
  2. customthe reaction
  3. customseparated by decantation
  4. washwashed again with water
  5. customThe brown solution obtained
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customis crystallized from isopropanol in order
  9. customto give
  10. filtrationafter filtration, 3426 g of brown crystals

出典と根拠

ORDレコード
ord-da48c8f1b19f419eb41a2cb3005a31a4
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07208603B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート