Water → 4-cyano-N-(4-propoxyphenylmethyl)piperidine

HRID 1683833ノート

反応式

HRID 1683833 の反応式
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)=O.[Cl-].[Na+].P(Cl)(Cl)(Cl)=O.O>ClCCCl>[C:2]([CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH3:20])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)#[N:1]

参加物

6

反応物 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 190409324-aminocarbonyl-N-(4-propoxyphenylmethyl)piperidine

生成物 1

HCID 190409134-cyano-N-(4-propoxyphenylmethyl)piperidine収率 56.1%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A mixture of 27.0 grams (0.10 mole) of 4-aminocarbonyl-N-(4-propoxyphenylmethyl)piperidine in 200 mL of 1,2-dichloroethane was stirred at ambient temperature, and 8.0 grams (0.14 mole) of sodium chloride, followed by 9.2 grams (0.06 mole) of phosphorous oxychloride were added. The reaction mixture was then warmed to reflux, where it stirred for about 1.75 hours. The reaction mixture was cooled to ambient temperature and about 350 mL of water was added. The aqueous layer was separated, washed with two portions of diethyl ether, and then made basic with aqueous 5% sodium hydroxide. The mixture was extracted with two portions of diethyl ether. The combined extracts were washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and poured through a pad of silica gel. The silica gel pad was washed with 1000 mL of diethyl ether. The combined eluants were concentrated under reduced pressure, yielding 14.5 grams of 4-cyano-N-(4-propoxyphenylmethyl)piperidine. The NMR spectrum was consistent with the proposed structure.

後処理

  1. additionwere added
  2. temperatureThe reaction mixture was then warmed
  3. temperatureto reflux
  4. stirringwhere it stirred for about 1.75 hours
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. customThe aqueous layer was separated
  7. washwashed with two portions of diethyl ether
  8. extractionThe mixture was extracted with two portions of diethyl ether
  9. washThe combined extracts were washed with an aqueous solution saturated with sodium chloride
  10. dry with materialThe organic layer was dried with sodium sulfate
  11. additionpoured through a pad of silica gel
  12. washThe silica gel pad was washed with 1000 mL of diethyl ether
  13. concentrationThe combined eluants were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3567f922159a472597fd18531e28a4a4
出典データセット
uspto-grants-1997_06
特許番号
US05639763

反応ノート

読み込み中…