Potassium Hydroxide → 1-Carbethoxy-4-methylamino-3-ethylpiperidine

HRID 746860ノート

反応式

HRID 746860 の反応式
Cl.CN.[C:4]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([CH2:16][CH3:17])[CH2:10]1)([O:6][CH2:7][CH3:8])=[O:5].[OH-].[K+].[C:20]([BH3-])#[N:21].[Na+]>CO>[C:4]([N:9]1[CH2:14][CH2:13][CH:12]([NH:21][CH3:20])[CH:11]([CH2:16][CH3:17])[CH2:10]1)([O:6][CH2:7][CH3:8])=[O:5]

参加物

6

反応物 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 222788511-Carbethoxy-3-ethyl-4-piperidone

生成物 1

HCID 222788831-Carbethoxy-4-methylamino-3-ethylpiperidine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

Methylamine hydrochloride (17 g, 252 mmol) was added to the stirred solution of 1-carbethoxy-3-ethyl-4-piperidone (10 g, 50 mmol) in methanol (150 ml) followed by 14.1 g (252 mmol) KOH. Stirring was continued for 3 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (4.72 g, 75 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 12 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH ˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give crude 1-carbethoxy-4-methylamino-3-ethylpiperidine. The obtained crude 1-carbethoxy-4-methylamino-3-ethylpiperidine was suspended in 7 M NaOH solution (50 ml), stirred at 110° C. for 230 hr, cooled, extracted with ethyl acetate, dried (Na2SO4) and concentrated to dryness to afford 4-methylamino-3-ethyl-piperidine. Yield 3.5 g (50%), C8H18N2, m/z 142 (M+1).

後処理

  1. temperatureCooling
  2. customwas removed after 10 min.
  3. customresulting mixture
  4. stirringwas stirred for 12 hr at ambient temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. customtriturated with water
  7. extractionextracted with ethyl acetate
  8. customto remove impurities
  9. extractionextracted with ethyl acetate
  10. extractionEthyl acetate extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-27b796d504b447b5a2df967b2884a569
出典データセット
uspto-grants-2008_07
特許番号
US07393957B2

反応ノート

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